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Synthesis 2009(6): 869-887  
DOI: 10.1055/s-0028-1087980
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Transformations of meso Bicyclic Hydrazines: Versatile Access to Functionalized Aminocyclopentanes

Chloée Bournaud, Florence Chung, Alejandro Pérez Luna, Morgane Pasco, Gauthier Errasti, Thomas Lecourt, Laurent Micouin*
Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l"Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques 4, av de l’Observatoire, 75270 Paris cedex 06, France
Fax: +33(1)43291403; e-Mail: laurent.micouin@parisdescartes.fr;
Weitere Informationen

Publikationsverlauf

Received 22 December 2008
Publikationsdatum:
02. März 2009 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Bicyclic hydrazines, prepared by cycloaddition of cyclopentadiene and diazo compounds, have great synthetic potential. Numerous asymmetric transformations of these building blocks have been developed, involving the electrophilicity of their strained double bond, ring-opening reactions or skeletal rearrangements. All these transformations are fully diastereoselective, and, in some cases­, enantioselective, enabling the preparation of a wide range of useful synthetic intermediates from a single precursor in a few synthetic steps.

1 Introduction

2 Preparation and Conformational Properties of Bicyclic
Hydrazines

3 Synthetic Transformations without Ring Fragmentation

3.1 Hydroboration

3.2 Hydroformylation and Halocarbomethoxylation

3.3 Dihydroxylation and Aminohydroxylation

3.4 Hydroarylation

3.5 Sequential Arylation-Alkynylation

3.6 Arylative Cyclization

3.7 Cyclopropanation

3.8 Pauson-Khand Reaction

3.9 Cycloaddition Reactions

4 Synthetic Transformations with Ring Fragmentation

4.1 Palladium-Catalyzed Ring-Opening Reactions

4.2 Copper-Catalyzed Ring-Opening Reactions

4.3 Rhodium-Catalyzed Ring-Opening Reactions

4.4 Ruthenium-Catalyzed Ring-Opening-Metathesis Reactions and Oxidative Cleavage

5 Rearrangements

5.1 Rearrangements Involving Allylic Cations

5.2 Rearrangements Involving Aziridiniums

6 Synthetic Applications

7 Conclusion

Key words

asymmetric synthesis - bicyclic hydrazines - ring-opening­ reactions - amines - asymmetric catalysis

    References

  • 1 Diels O. Alder K. Liebigs Ann. Chem.  1928,  460:  98 
    Google Scholar
  • 2 Diels O. Blom JH. Koll W. Liebigs Ann. Chem.  1925,  443:  242 
    CrossrefGoogle Scholar
  • 3a Roth WR. Martin M. Liebigs Ann. Chem.  1967,  702:  1 
    Google Scholar
  • 3b Roth WR. Martin M. Tetrahedron Lett.  1967,  4695 
    Google Scholar
  • 3c Allred EL. Smith RL. J. Am. Chem. Soc.  1967,  89:  7133 
    Google Scholar
  • 4 Little D. Chem. Rev.  1986,  86:  875 
    CrossrefGoogle Scholar
  • 5a Engel PS. Chem. Rev.  1980,  80:  99 
    Google Scholar
  • 5b Simpson CJSM. Wilson GJ. Adam WJ. J. Am. Chem. Soc.  1991,  113:  4728 
    Google Scholar
  • 5c Reyes MB. Carpenter BK. J. Am. Chem. Soc.  2000,  122:  10163 
    Google Scholar
  • 5d Khuong KS. Houk KN. J. Am. Chem. Soc.  2003,  125:  14867 
    Google Scholar
  • 5e Adam W. Diedering M. Trofimov AV. J. Phys. Org. Chem.  2004,  17:  643 
    Google Scholar
  • 5f Abe M. Ishihara C. Kawanami S. . J. Am. Chem. Soc.  2005,  127:  10 
    Google Scholar
  • 6 Spandl RJ. Bender A. Spring DR. Org. Biomol. Chem.  2008,  6:  1149 
    CrossrefPubMedGoogle Scholar
  • 7 Eliel EL. Wilen SH. Stereochemistry of Organic Compounds   Wiley; New York: 1994.  p.758 
    Google Scholar
  • 8 Hoffman RW. Angew. Chem. Int. Ed.  2003,  42:  1096 
    CrossrefPubMedGoogle Scholar
  • 9 Houben-Weyl Methods of Organic Synthesis   4th ed., Vol. E21:  Helmchen G. Hoffmann RW. Mulzer E. Thieme; Stuttgart: 1995.  p.5451 
    Google Scholar
  • 10 Needleman SB. Kuo CC. Chem. Rev.  1962,  62:  405 
    CrossrefGoogle Scholar
  • 11 MacKenzie JCJ. Rodgmen A. Wright GF. J. Org. Chem.  1952,  17:  1666 
    CrossrefGoogle Scholar
  • 12 Gassman PG. Mansfield KT. Org. React.  1969,  49:  1 
    Google Scholar
  • 13 Stout DM. Takaya T. Meyers AI. J. Org. Chem.  1975,  40:  563 
    CrossrefGoogle Scholar
  • 14 Carpino LA. Terry PH. Crowley PJ. J. Org. Chem.  1961,  26:  4336 
    CrossrefGoogle Scholar
  • 15 Heyman ML. Snyder JP. Tetrahedron Lett.  1973,  2859 
    CrossrefGoogle Scholar
  • 16 Masamune S. Nakamura N. Spadaro J. J. Am. Chem. Soc.  1975,  97:  918 
    CrossrefGoogle Scholar
  • 17 Adam W. Berkessel A. Chem. Ber.  1985,  118:  5018 
    CrossrefGoogle Scholar
  • 18 Houben-Weyl Methods of Organic Synthesis   4th ed., Vol. E21:  Helmchen G. Hoffmann RW. Mulzer E. Thieme; Stuttgart: 1995.  p.5469 
    Google Scholar
  • 19a Gillis BT. Hagarty JD. J. Org. Chem.  1967,  32:  330 
    Google Scholar
  • 19b Cookson RC. Gilani SSH. Stevens IDR. J. Chem. Soc. C  1967,  1905 
    Google Scholar
  • 19c Moore JA. Muth R. Sorace R. J. Org. Chem.  1974,  39:  3799 
    Google Scholar
  • 19d Snyder JP. Bandurco VT. Darack F. Olsen H. J. Am. Chem. Soc.  1974,  96:  5158 
    Google Scholar
  • 19e Warmhoff H. Kunz G. Angew. Chem. Int. Ed.  1981,  20:  797 
    Google Scholar
  • 20 Corey EJ. Snider BB. J. Org. Chem.  1973,  38:  3632 
    CrossrefGoogle Scholar
  • 21a Nelsen SF. Hollinsed WC. Grezzo LA. Parmelee WP. J. Am. Chem. Soc.  1979,  101:  7347 
    Google Scholar
  • 21b Kealy TJ. J. Am. Chem. Soc.  1962,  84:  966 
    Google Scholar
  • 22 Campbell JA. Mackay D. Sauer TD. Can. J. Chem.  1972,  50:  1568 
    CrossrefGoogle Scholar
  • 23 Miesel JL. Tetrahedron Lett.  1974,  15:  3847 
    CrossrefGoogle Scholar
  • 24 Agmon I. Kaftory M. Nelsen SF. Blackstock SC. J. Am. Chem. Soc.  1986,  108:  4477 
    Google Scholar
  • 25 Pandey B. Athawale AA. Reddy RS. Chem. Lett.  1991,  1173 
    CrossrefGoogle Scholar
  • 26 Anderson JE. Lehn J.-M. Tetrahedron  1968,  24:  123 
    CrossrefGoogle Scholar
  • 27a Nomura Y. Masai N. Takeguchi Y. J. Chem. Soc., Chem. Commun.  1974,  307 
    Google Scholar
  • 27b

    Pérez Luna, A.; unpublished results.

  • 28 Allred EL. Anderson CL. Smith RL. Tetrahedron Lett.  1966,  9:  951 
    Google Scholar
  • 29 Allred EL. Smith RL. J. Org. Chem.  1966,  31:  3498 
    CrossrefGoogle Scholar
  • 30 Allred EL. Anderson CL. Smith RL. J. Org. Chem.  1966,  31:  3493 
    CrossrefGoogle Scholar
  • 31a Burgess K. Ohlmeyer MJ. Chem. Rev.  1991,  91:  1179 
    Google Scholar
  • 31b Beletskaya I. Pelter A. Tetrahedron  1997,  53:  4957 
    Google Scholar
  • 31c Hayashi T. In Comprehensive Asymmetric Catalysis   Jacobsen EN. Pfaltz A. Yamamoto H. Springer-Verlag; Berlin: 1999. 
    Google Scholar
  • 31d Crudden CM. Edwards D. Eur. J. Org. Chem.  2003,  4695 
    Google Scholar
  • 31e Caroll A.-M. O’Sullivan TP. Guiry PJ. Adv. Synth. Catal.  2005,  347:  609 
    Google Scholar
  • 32a Burgess K. Ohlmeyer MJ. J. Org. Chem.  1988,  53:  5178 
    Google Scholar
  • 32b Hayashi T. Matsumoto Y. Ito Y. J. Am. Chem. Soc.  1989,  111:  3426 
    Google Scholar
  • 32c Sato M. Miyaura N. Suzuki A. Tetrahedron Lett.  1990,  31:  231 
    Google Scholar
  • 32d Brown JM. Lloyd-Jones GC. Tetrahedron: Asymmetry  1991,  1:  869 
    Google Scholar
  • 32e Hayashi T. Matsumoto Y. Ito Y. Tetrahedron: Asymmetry  1991,  2:  601 
    Google Scholar
  • 32f Burgess K. Van der Donk WA. Ohlmeyer MJ. Tetrahedron: Asymmetry  1991,  2:  613 
    Google Scholar
  • 32g Zhang J. Lou B. Guo G. Dai L. J. Org. Chem.  1991,  56:  1670 
    Google Scholar
  • 32h Brown JM. Hulmer DI. Langzell TP. J. Chem. Soc., Chem. Commun.  1993,  1673 
    Google Scholar
  • 32i Togni A. Breutel C. Schnyder A. Spindler F. Landert H. Tijani A. J. Am. Chem. Soc.  1994,  116:  4062 
    Google Scholar
  • 32j Schnyder A. Hintermann L. Togni A. Angew. Chem., Int. Ed. Engl.  1995,  34:  931 
    Google Scholar
  • 32k Doucet H. Fernandez E. Layzell TP. Brown JM. Chem. Eur. J.  1999,  5:  1320 
    Google Scholar
  • 32l Brunel J.-M. Buono G. Tetrahedron Lett.  1999,  40:  3561 
    Google Scholar
  • 32m Fernandez E. Maeda K. Hooper MW. Brown JM. Chem. Eur. J.  2000,  6:  1840 
    Google Scholar
  • 32n McCarthy M. Guiry P. Polyhedron  2000,  19:  541 
    Google Scholar
  • 32o Demay S. Volant F. Knochel P. Angew. Chem., Int. Ed.  2001,  40:  1235 
    Google Scholar
  • 33 Pérez Luna A. Ceschi M.-A. Bonin M. Micouin L. Husson H.-P. J. Org. Chem.  2002,  67:  3522 
    CrossrefPubMedGoogle Scholar
  • 34 Bunlaksananusorn T. Polborn K. Knochel P. Angew. Chem. Int. Ed.  2003,  42:  3941 
    CrossrefPubMedGoogle Scholar
  • 37 Bournaud C. Thesis   Université Paris Descartes; France: 2006. a temperature-dependent inversion of enantioselectivity has been observed with pinacolborane in DME (but not in THF)
    Google Scholar
  • 38a Evans DA. Fu GC. Hoveyda AH. J. Am. Chem. Soc.  1992,  114:  6671 
    Google Scholar
  • 38b Westcott SA. Marder TB. Organometallics  1993,  12:  975 
    Google Scholar
  • 39 Pérez Luna A. Bonin M. Micouin L. Husson H.-P. J. Am. Chem. Soc.  2002,  124:  12098 
    Google Scholar
  • 40 Bunlaksananusorn T. Pérez Luna A. Bonin M. Micouin L. Knochel P. Synlett  2003,  2240 
    Artikel in Thieme ConnectGoogle Scholar
  • 41 Alexakis A. Polet D. Bournaud C. Bonin M. Micouin L. Tetrahedron: Asymmetry  2005,  16:  3672 
    CrossrefGoogle Scholar
  • 42a Crudden CM. Hleba YB. Chen AC. J. Am. Chem. Soc.  2004,  126:  9200 
    Google Scholar
  • 42b Black A. Brown JM. Pichon C. Chem. Commun.  2005,  5284 
    Google Scholar
  • 42c Edwards DR. Hleba YB. Lata CJ. Calhoun LA. Crudden CM. Angew. Chem. Int. Ed.  2007,  46:  7799 
    Google Scholar
  • 43a Consiglio G. Morandini F. Scalone P. Pino P. J. Organomet. Chem.  1985,  279:  195 
    Google Scholar
  • 43b Parrinello G. Deschenaux R. Stille JK. J. Org. Chem.  1986,  51:  4189 
    Google Scholar
  • 43c Parrinello G. Stille JK. J. Am. Chem. Soc.  1987,  109:  7122 
    Google Scholar
  • 43d Lu S. Li X. Wang A. Catalysis Today  2000,  63:  531 
    Google Scholar
  • 43e Huang J. Bunel E. Allgeier A. Tedrow J. Storz T. Preston J. Correl T. Manley D. Soukup T. Jensen R. Syed R. Moniz G. Larsen R. Martinelli M. Reider PJ. Tetrahedron Lett.  2005,  46:  7831 
    Google Scholar
  • 44 Wilson RM. Schnapp KA. Merwin RK. Ranganathan R. Moats DL. Conrad TT. J. Org. Chem.  1986,  51:  4028 
    CrossrefGoogle Scholar
  • 45 Bournaud C. Lecourt T. Micouin L. Méliet C. Agbossou-Niedercorn F. Eur. J. Org. Chem.  2008,  2298 
    CrossrefGoogle Scholar
  • 46 Ham S.-W. Chang W. Dowd P. J. Am. Chem. Soc.  1989,  111:  4130 
    CrossrefGoogle Scholar
  • 47a Mellor JM. Smith NM. J. Chem. Soc., Perkin Trans. 1  1984,  2927 
    Google Scholar
  • 47b Grabowski S. Armbruster J. Prinzbach H. Tetrahedron Lett.  1997,  38:  5485 
    Google Scholar
  • 47c Micouin L, Dardel F, Tisné-Vicrobeck C, Maurice F, Bonin M, Bournaud C, and Bégis G. inventors; WO 2006/024784  A2. 
  • 48 Kolb HC. Sharpless BK. In Transition Metals for Organic Synthesis   2nd ed., Vol. 2:  Beller M. Bolm C. Wiley-VCH; Weinheim: 2004.  p.309 
    Google Scholar
  • 50 Storsberg J. Nandakumar MV. Sankaranarayanan S. Kaufmann DE. Adv. Synth. Catal.  2001,  343:  177 
    CrossrefGoogle Scholar
  • 51a Kaufmann DE, Nandakumar MV, and Storsberg J. inventors; WO 02/36528  A2.  ; Incorrect structural assignments have been reported several times in this area, mainly because of the low resolution of NMR spectra caused by several rotameric species
  • 51b Yao M.-L. Adiwidjaja G. Kaufmann DE. Angew. Chem. Int. Ed.  2002,  41:  3375 
    Google Scholar
  • 52 Menard F. Lautens M. Angew. Chem. Int. Ed.  2008,  47:  2085 
    CrossrefGoogle Scholar
  • 53 Catellani M. Motti E. Della Ca’ N. Acc. Chem. Res.  2008,  41:  1512 
    CrossrefPubMedGoogle Scholar
  • 54 Lautens M. Mancuso J. J. Org. Chem.  2004,  69:  3478 
    CrossrefPubMedGoogle Scholar
  • 55 Tseng N.-W. Mancuso J. Lautens M. J. Am. Chem. Soc.  2006,  128:  5338 
    CrossrefPubMedGoogle Scholar
  • 56 Tenaglia A. Marc S. J. Org. Chem.  2006,  71:  3569 
    CrossrefPubMedGoogle Scholar
  • 57 Bigeault J. Giordano L. de Riggi I. Gimbert Y. Buono G. Org. Lett.  2007,  9:  3567 
    Google Scholar
  • 58a Allred EL. Hinshaw JC. Johnson AL. J. Am. Chem. Soc.  1969,  91:  3382 
    Google Scholar
  • 58b Olsen H. Snyder JP. J. Am. Chem. Soc.  1977,  99:  1524 
    Google Scholar
  • 59 Pauson PL. Khand IU. Ann. N. Y. Acad. Sci.  1977,  295:  2 
    CrossrefGoogle Scholar
  • 60 Derdau V. Laschat S. J. Organomet. Chem.  2002,  642:  131 
    CrossrefGoogle Scholar
  • 61a Warrener RN. Bina S. Butler DN. Pitt IG. Russel RA. Tetrahedron Lett.  1990,  31:  7073 
    Google Scholar
  • 61b Warrener RN. Pitt IG. Nunn EE. Tetrahedron Lett.  1994,  35:  621 
    Google Scholar
  • 62a Huisgen R. Stangle H. Sturm HJ. Wagenhofer H. Angew. Chem.  1961,  73:  170 
    Google Scholar
  • 62b Huisgen R. Moebius L. Mueller G. Stangl H. Szeimies G. Vernon JM. Chem. Ber.  1965,  98:  3992 
    Google Scholar
  • 62c Wade PA. Hinney HR. J. Am. Chem. Soc.  1979,  101:  1319 
    Google Scholar
  • 62d Rieber N, Boehm H, Platz R, and Fuchs W. inventors; EP 0046188  A1. 
  • 62e Rieber N, Platz R, and Fuchs W. inventors; EP 0046192  A1. 
  • 62f Aitken RA. Carcas K. Hill L. Massil T. Raut SV. Tetrahedron Lett.  1997,  53:  2261 
    Google Scholar
  • 63 Kuderna JG. Sims JW. Wikstrom JF. Soloway SB. J. Am. Chem. Soc.  1959,  81:  382 
    CrossrefGoogle Scholar
  • 64 Sajisha VS. Smitha M. Anas S. Radhakrishnan KV. Tetrahedron  2006,  62:  3997 
    CrossrefGoogle Scholar
  • 65a Radhakrishnan KV. Sajisha VS. Anas S. Krishnan KS. Synlett  2005,  2273 
    Google Scholar
  • 65b Sajisha VS. Radhakrishnan KV. Adv. Synth. Catal.  2006,  348:  924 
    Google Scholar
  • 66a John J. Sajisha VS. Mohanlal S. Radhakrishnan KV. Chem. Commun.  2006,  3510 
    Google Scholar
  • 66b Anas S. John J. Sajisha VS. John J. Rajan R. Suresh E. Radhakrishnan KV. Org. Biomol. Chem.  2007,  5:  4010 
    Google Scholar
  • 67 John J. Anas S. Sajisha VS. Viji S. Radhakrishnan KV. Tetrahedron Lett.  2007,  48:  7225 
    CrossrefGoogle Scholar
  • For related examples, see:
  • 68a Bourgeois-Cury A. Doan D. Goré J. Tetrahedron Lett.  1992,  33:  1277 
    Google Scholar
  • 68b Alonso DA. Bertilsson SK. Johnsson SY. Nordin SJM. Södergren MJ. Andersson PG. J. Org. Chem.  1999,  64:  2276 
    Google Scholar
  • 68c Miller A. Procter G. Tetrahedron Lett.  1990,  31:  1043 
    Google Scholar
  • 68d Mulvihill MJ. Surman MD. Miller MJ. J. Org. Chem.  1998,  63:  4874 
    Google Scholar
  • 68e Surman MD. Miller MJ. Org. Lett.  2001,  3:  519 
    Google Scholar
  • 68f Cowart M. Bennett MJ. Kerwin JF. J. Org. Chem.  1999,  64:  2240 
    Google Scholar
  • 69 Pérez Luna A. Cesario M. Bonin M. Micouin L. Org. Lett.  2003,  5:  4771 
    CrossrefGoogle Scholar
  • 70 Modern Organocopper Chemistry   Krause N. Wiley-VCH; Weinheim: 2002. 
    Google Scholar
  • 71 Pineschi M. Del Moro F. Crotti P. Macchia F. Org. Lett.  2005,  7:  3605 
    CrossrefPubMedGoogle Scholar
  • 72 Bournaud C. Falciola C. Lecourt T. Rosset S. Alexakis A. Micouin L. Org. Lett.  2006,  8:  3581 
    CrossrefGoogle Scholar
  • 73 Palais L. Mikhel IS. Bournaud C. Micouin L. Falciola CA. Vuagnoux-d’Augustin M. Rosset S. Bernardinelli G. Alexakis A. Angew. Chem. Int. Ed.  2007,  46:  7462 
    CrossrefGoogle Scholar
  • 74 Bertolini F. Macchia F. Pineschi M. Tetrahedron Lett.  2006,  47:  9173 
    CrossrefGoogle Scholar
  • 75 Crotti S. Bertolini F. Macchia F. Pineschi M. Chem. Commun.  2008,  3127 
    CrossrefGoogle Scholar
  • 76 Menard F. Weise CF. Lautens M. Org. Lett.  2007,  9:  5365 
    CrossrefGoogle Scholar
  • 77 Ellis JM. King SB. Tetrahedron Lett.  2002,  43:  5833 
    CrossrefGoogle Scholar
  • 78 Van Velduizen JJ. Gillingham DG. Garber SB. Kataoka O. Hoveyda AH. J. Am. Chem. Soc.  2003,  125:  12502 
    Google Scholar
  • 79 Berlin JM. Goldberg SD. Grubbs RH. Angew. Chem. Int. Ed.  2006,  45:  7591 
    CrossrefGoogle Scholar
  • 80a Arakawa Y. Goto T. Kawase K. Yoshifuji S. Chem. Pharm. Bull.  1995,  43:  535 
    Google Scholar
  • 80b Arakawa Y. Goto T. Kawase K. Yoshifuji S. Chem. Pharm. Bull.  1998,  46:  674 
    Google Scholar
  • 81 Frauenrath H. Houben-Weyl Methods of Organic Synthesis   4th ed., Vol. E21:  Helmchen G. Hoffmann RW. Mulzer E. Thieme; Stuttgart: 1995.  p.3671 
    Google Scholar
  • 82a Mackay D. Campbell JA. Jennison CPR. Can. J. Chem.  1970,  48:  81 
    Google Scholar
  • 82b Campbell JA. Mackay D. Sauer TD. Can. J. Chem.  1972,  50:  371 
    Google Scholar
  • 82c Chung CY.-J. Mackay D. Sauer TD. Can. J. Chem.  1972,  50:  3315 
    Google Scholar
  • 82d Chung CY.-J. Mackay D. Sauer TD. Can. J. Chem.  1972,  50:  1568 
    Google Scholar
  • 83 Dao LH. Mackay D. Can. J. Chem.  1978,  56:  1724 
    CrossrefGoogle Scholar
  • 84 Martins A. Lemouzy S. Lautens M. Org. Lett.  2009,  11:  181 
    CrossrefPubMedGoogle Scholar
  • 85a Raasch MS. J. Org. Chem.  1975,  40:  161 
    Google Scholar
  • 85b Offereins B. Altona C. Romers C. Acta Crystallogr., Sect. B  1973,  29:  2098 
    Google Scholar
  • 86 Bournaud C. Bonin M. Micouin L. Org. Lett.  2006,  8:  3041 
    CrossrefPubMedGoogle Scholar
  • 87 Feuvrie C. Blanchet J. Bonin M. Micouin L. Org. Lett.  2004,  6:  2333 
    CrossrefPubMedGoogle Scholar
  • 88 Bournaud C. Robic D. Bonin M. Micouin L. J. Org. Chem.  2005,  70:  3316 
    CrossrefPubMedGoogle Scholar
  • 89 Chung F. Tisné C. Lecourt T. Dardel F. Micouin L. Angew. Chem. Int. Ed.  2007,  46:  4489 
    CrossrefPubMedGoogle Scholar
  • 90 Lombès T. Bégis G. Maurice F. Turcaud S. Lecourt T. Dardel F. Micouin L. ChemBioChem  2008,  9:  1368 
    CrossrefPubMedGoogle Scholar
35

The low reactivity and selectivity observed with the QUINAP ligand could arise from the lower stability of the catalytic species generated from neutral rhodium precatalyst (Prof. J. M. Brown, personal communication to L.M.). Cationic rhodium sources have not been evaluated with this ligand in this study.

36

Pérez Luna, A.; unpublished results.

49

Bournaud, C.; unpublished results.