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Synlett 2011(6): 787-790  
DOI: 10.1055/s-0030-1259689
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Tandem Olefin Migration-Aldol Condensation in Water with an Amphiphilic Resin-Supported Ruthenium Complex

Yohei Oe, Yasuhiro Uozumi*
Institute for Molecular Science (IMS), Higashiyama 5-1, Myodaiji, Okazaki 444-8787, Japan
Fax: +81(564)595574; e-Mail: uo@ims.ac.jp;
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Publikationsverlauf

Received 15 December 2010
Publikationsdatum:
25. Februar 2011 (online)

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Abstract

A catalytic tandem olefin migration-aldol condensation process with allylic carbinols and aryl aldehydes was performed with 0.5 mol% of an amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin supported phosphine-ruthenium complex in water as a single reaction medium under heterogeneous conditions to give the corresponding aldols with syn selectivity. Inverse stereoselectivity (anti selectivity) was observed when the reaction was carried out in the presence of K2CO3.

Key words

tandem reaction - aldol condensation - aqueous media - polymer support - ruthenium catalyst

    References and Notes

  • For reviews on aqueous switching of organic transformations, see:
  • 2a Li C.-J. Chan T.-H. Organic Reactions in Aqueous Media   Wiley-VCH; New York: 1997. 
    Google Scholar
  • 2b Grieco PA. Organic Synthesis in Water   Kluwer Academic Publishers; Dordrecht: 1997. 
    Google Scholar
  • 2c Herrmann WA. Kohlpaintner CW. Angew. Chem., Int. Ed. Engl.  1993,  32:  1524 
    Google Scholar
  • 2d Lindström UM. Chem. Rev.  2002,  102:  2751 
    Google Scholar
  • 2e Commentary: Uozumi Y. Synlett  2010,  1988 
    Google Scholar
  • For reviews on heterogeneous switching of organic transformations, see:
  • 3a Bailey DC. Langer SH. Chem. Rev.  1981,  81:  109 
    Google Scholar
  • 3b Shuttleworth SJ. Allin SM. Sharma PK. Synthesis  1997,  1217 
    Google Scholar
  • 3c Shuttleworth SJ. Allin SM. Wilson RD. Nasturica D. Synthesis  2000,  1035 
    Google Scholar
  • 3d Dörwald FZ. Organic Synthesis on Solid Phase   Wiley-VCH; Weinheim: 2000. 
    Google Scholar
  • 3e Leadbeater NE. Marco M. Chem. Rev.  2002,  102:  3217 
    Google Scholar
  • 3f Ley SV. Baxendale IR. Bream RN. Jackson PS. Leach AG. Longbottom DA. Nesi M. Scott JS. Storer RI. Taylor SJ. J. Chem. Soc., Perkin Trans. 1  2000,  3815 
    Google Scholar
  • 3g McNamara CA. Dixon MJ. Bradley M. Chem. Rev.  2002,  102:  3275 
    Google Scholar
  • 3h Chiral Catalyst Immobilization and Recycling   De Vos DE. Vankelecom IFJ. Jacobs PA. Wiley-VCH; Weinheim: 2000. 
    Google Scholar
  • 3i Fan Q.-H. Li Y.-M. Chan ASC. Chem. Rev.  2002,  102:  3385 
    Google Scholar
  • 3j Uozumi Y. Top. Curr. Chem.  2004,  242:  77 
    Google Scholar
  • 3k Guino M. Hii KKM. Chem. Soc. Rev.  2007,  36:  608 
    Google Scholar
  • 3l Wang Z. Chen G. Ding K. Chem. Rev.  2009,  109:  322 
    Google Scholar
  • 3m Lu J. Toy PH. Chem. Rev.  2009,  109:  815 
    Google Scholar
  • 4a Bayer E. Rapp W. In Chemistry of Peptides and Proteins   Vol. 3:  Voelter W. Bayer E. Ovchinikov YA. Iwanov VT. Walter de Gruter; Berlin: 1986.  p.3 
    Google Scholar
  • 4b Rapp W. In Combinatorial Peptide and Nonpeptide Libraries   Jung G., VCH; Weinheim: 1996.  p.425 
    Google Scholar
  • For studies on polymer-supported transition-metal-complex catalysts from the author’s group, see for allylic substitution:
  • 5a Uozumi Y. Danjo H. Hayashi T. Tetrahedron Lett.  1997,  38:  3557 
    Google Scholar
  • 5b Danjo H. Tanaka D. Hayashi T. Uozumi Y. Tetrahedron  1999,  55:  14341 
    Google Scholar
  • Cross-coupling:
  • 5c Uozumi Y. Danjo H. Hayashi T.
    J. Org. Chem.  1999,  64:  3384 
    Google Scholar
  • Carbonylation reaction:
  • 5d Uozumi Y. Watanabe T. J. Org. Chem.  1999,  64:  6921 
    Google Scholar
  • Suzuki-Miyaura coupling:
  • 5e Uozumi Y. Nakai Y. Org. Lett.  2002,  4:  2997 
    Google Scholar
  • Heck reaction:
  • 5f Uozumi Y. Kimura T. Synlett  2002,  2045 
    Google Scholar
  • Asymmetric alkylation:
  • 5g Uozumi Y. Shibatomi K. J. Am. Chem. Soc.  2001,  123:  2919 
    Google Scholar
  • Asymmetric amination:
  • 5h Uozumi Y. Tanaka H. Shibatomi K. Org. Lett.  2004,  6:  281 
    Google Scholar
  • Asymmetric catalysis:
  • 5i Hocke H. Uozumi Y. Synlett  2002,  2049 
    Google Scholar
  • Rh catalysis:
  • 5j Uozumi Y. Nakazono M. Adv. Synth. Catal.  2002,  344:  274 
    Google Scholar
  • Asymmetric catalysis:
  • 5k Hocke H. Uozumi Y. Tetrahedron  2003,  59:  619 
    Google Scholar
  • 5l Hocke H. Uozumi Y. Tetrahedron  2004,  60:  9297 
    Google Scholar
  • Asymmetric cycloisomerization:
  • 5m Nakai Y. Uozumi Y. Org. Lett.  2005,  7:  291 
    Google Scholar
  • Cross-coupling:
  • 5n Uozumi Y. Kikuchi M. Synlett  2005,  1775 
    Google Scholar
  • Asymmetric etherification:
  • 5o Uozumi Y. Kimura M. Tetrahedron: Asymmetry  2006,  17:  161 
    Google Scholar
  • Asymmetric alkylation:
  • 5p Kobayashi Y. Tanaka D. Danjo H. Uozumi Y. Adv. Synth. Catal.  2006,  348:  1561 
    Google Scholar
  • Allylic azidation:
  • 5q Uozumi Y. Suzuka T. Kawade R. Takenaka H. Synlett  2006,  2109 
    Google Scholar
  • Nitromethylation:
  • 5r Uozumi Y. Suzuka T. J. Org. Chem.  2006,  71:  8644 
    Google Scholar
  • Allylic sulfonylation:
  • 5s Uozumi Y. Suzuka T. Synthesis  2008,  1960 
    Google Scholar
  • Asymmetric desymmetrization:
  • 5t Uozumi Y. Takenaka H. Suzuka T. Synlett  2008,  1557 
    Google Scholar
  • Asymmetric Suzuki coupling:
  • 5u Uozumi Y. Matsuura Y. Arakawa T. Yamada YMA. Angew. Chem. Int. Ed.  2009,  48:  2708 
    Google Scholar
  • Pt-catalyzed oxidation:
  • 5v Yamada YMA. Arakawa T. Hocke H. Uozumi Y. Chem. Asian J.  2009,  4:  1092 
    Google Scholar
  • Sonogahsira coupling:
  • 5w Suzuka T. Okada Y. Ooshiro K. Uozumi Y. Tetrahedron  2010,  66:  1064 
    Google Scholar
  • Buchwald-Hartwig reaction:
  • 5x Hirai Y. Uozumi Y. Chem. Commun.  2010,  46:  1103 
    Google Scholar
  • 5y Hirai Y. Uozumi Y. Chem. Asian J.  2010,  5:  1788 
    Google Scholar
  • 6 Kharasch reaction: Oe Y. Uozumi Y. Adv. Synth. Catal.  2008,  350:  1771 
    CrossrefGoogle Scholar
  • For examples of amphiphilic polymer-supported ruthenium complexes, see:
  • 7a Kayaki Y. Shimokawatoko Y. Ikariya T. Adv. Synth. Catal.  2003,  345:  175 
    Google Scholar
  • 7b Judkins CMG. Knights KA. Johnson BFG. De Miguel YR. Raja R. Thomas JM. Chem. Commun.  2001,  2624 
    Google Scholar
  • In water:
  • 8a Wang M. Li CJ. Tetrahedron Lett.  2002,  43:  3589 
    Google Scholar
  • In ionic liquid:
  • 8b Yang X.-F. Wang M. Varma RS. Li C.-J. Org. Lett.  2003,  5:  657 
    Google Scholar
  • In aqueous organic media:
  • 8c Wang M. Yang X.-F. Li C.-J. Eur. J. Org. Chem.  2003,  998 
    Google Scholar
  • 8d Yang X.-F. Wang M. Varma RS. Li C.-J. J. Mol. Catal. A: Chem.  2004,  214:  147 
    Google Scholar
  • Rh catalysis:
  • 9a Gazzard LJ. Motherwell WB. Sandham DA. J. Chem. Soc., Perkin Trans. 1  1999,  979 
    Google Scholar
  • Fe:
  • 9b Crévisy N. Wietrich M. Le Boulaire V. Uma R. Grée R. Tetrahedron Lett.  2001,  42:  395 
    Google Scholar
  • 9c Uma R. Gouault N. Crévisy N. Grée R. Tetrahedron Lett.  2003,  43:  6187 
    Google Scholar
  • Ni:
  • 9d Cuperly D. Crévisy N. Grée R. Synlett  2004,  93 
    Google Scholar
  • 9e Cuperly D. Petrignet J. Crévisy N. Grée R. Chem. Eur. J.  2006,  12:  3261 
    Google Scholar
1

Present address: Graduate School Division of Engineering, Doshisha University; yoe@mail.doshisha.ac.jp.