Organocatalytic Domino Double
Michael Reaction of Ethyl (E)-7-Oxohept-2-enoate
and α,β-Unsaturated Aldehydes: Efficient Asymmetric
Synthesis of Cyclohexanes with Four Contiguous Stereocenters

Bor-Cherng Hong; Amit A. Sadani; Roshan Y. Nimje; Nitin S. Dange; Gene-Hsiang Lee

doi:10.1055/s-0030-1260469

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Synthesis 2011(12): 1887-1895
DOI: 10.1055/s-0030-1260469

PAPER

Organocatalytic Domino Double Michael Reaction of Ethyl (E)-7-Oxohept-2-enoate and α,β-Unsaturated Aldehydes: Efficient Asymmetric Synthesis of Cyclohexanes with Four Contiguous Stereocenters

Bor-Cherng Hong*^a, Amit A. Sadani^a, Roshan Y. Nimje^a, Nitin S. Dange^a, Gene-Hsiang Lee^b
^a Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan, R.O.C.
Fax: +886(5)2721040; e-Mail: chebch@ccu.edu.tw;
^b Instrumentation Center, National Taiwan University, Taipei, 106, Taiwan, R.O.C.

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Publikationsverlauf

Received 14 March 2011
Publikationsdatum:
16. Mai 2011 (online)

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Abstract

Organocatalytic domino double Michael reactions of ethyl (E)-7-oxohept-2-enoate and α,β-unsaturated aldehydes provided ethyl 2-(2,4-diformyl-3-phenylcyclohexyl)acetate with excellent diastereoselectivities (>20:1 dr) and enantioselectivities (>99% ee). The adducts were further transformed to octahydro-3H-2-benzopyran-3-ones, octahydroisoquinolin-3(2H)-ones, and decahydro-5H-oxazolo[2,3-a]isoquinolin-5-ones.

Key words

Michael addition - aldehydes - organocatalysis - aldol reaction - quinolines

Supporting Information

References

For recent reviews:, see:
1a Vicario JL. Badía D. Carrillo L. Etxebarria J. Reyes E. Ruiz N. Org. Prep. Proced. Int. 2005, 37: 513

Suche in Google Scholar
1b Janecki T. Kedzia J. Wasek T. Synthesis 2009, 1227
1c Nising CF. Brase S. Chem. Soc. Rev. 2008, 37: 1218

Suche in Google Scholar
1d Enders D. Saint-Dizier A. Lannou M.-I. Lenzen A. Eur. J. Org. Chem. 2006, 29
1e Berner OM. Tedeschi L. Enders D. Eur. J. Org. Chem. 2002, 1877
1f Krause N. Hoffmann-Roder A. Synthesis 2001, 171
2a
See ref. 1d.
2b Xu LW. Xia CG. Eur. J. Org. Chem. 2005, 633
2c Enders D. Wang C. Liebich LX. Chem. Eur. J. 2009, 15: 11058

Suche in Google Scholar
2d Vicario JL. Badia D. Carrillo L. Synthesis 2007, 2065
2e Enders D. Luttgen K. Narine AA. Synthesis 2007, 959
2f Notz W. Tanaka F. Barbas CF. Acc. Chem. Res. 2004, 37: 580

Suche in Google Scholar
2g Guillena G. Najera C. Ramon DJ. Tetrahedron: Asymmetry 2007, 18: 2249

Suche in Google Scholar
2h Zlotin SG. Kucherenko AS. Beletskaya IP. Russ. Chem. Rev. (Engl. Transl.) 2009, 78: 737

Suche in Google Scholar
For recent reviews, see:
3a Grondal C. Jeanty M. Enders D. Nat. Chem. 2010, 2: 167

Suche in Google Scholar
For recent examples, see:
3b Ren QA. Gao YJ. Wang JA. Chem. Eur. J. 2010, 16: 13594

Suche in Google Scholar
3c Wang X.-F. Hua Q.-L. Cheng Y. An X.-L. Yang Q.-Q. Chen J.-R. Xiao W.-J. Angew. Chem. Int. Ed. 2010, 49: 8379

Suche in Google Scholar
3d Alemán J. Núñez A. Marzo L. Marcos V. Alvarado C. Ruano JLG. Chem. Eur. J. 2010, 16: 9453

Suche in Google Scholar
3e Enders D. Schmid B. Erdmann N. Raabe G. Synthesis 2010, 2271
3f Rueping M. Kuenkel A. Frohlich R. Chem. Eur. J. 2010, 16: 4173

Suche in Google Scholar
3g Zhang XS. Zhang SL. Wang W. Angew. Chem. Int. Ed. 2010, 49: 1481

Suche in Google Scholar
For a review of natural product synthesis using multicomponent reaction strategies, see:
4a Touré BB. Hall DG. Chem. Rev. 2009, 109: 4439

Suche in Google Scholar
Selected examples:
4b Zhang B. Cai L. Song H. Wang Z. He Z. Adv. Synth. Catal. 2010, 352: 97

Suche in Google Scholar
4c Reyes E. Talavera G. Vicario JL. Badía D. Carrillo L. Angew. Chem. Int. Ed. 2009, 48: 5701

Suche in Google Scholar
4d Zhang F.-L. Xu A.-W. Gong Y.-F. Wei M.-H. Yang X.-L. Chem. Eur. J. 2009, 15: 6815

Suche in Google Scholar
4e Hayashi Y. Okano T. Aratake S. Hazelard D. Angew. Chem. Int. Ed. 2007, 46: 4922

Suche in Google Scholar
4f Ramachary DB. Barbas CF. Chem. Eur. J. 2004, 10: 5323

Suche in Google Scholar
4g Jiang H. Nielsen JB. Nielsen M. Jørgensen KA. Chem. Eur. J. 2007, 13: 9068

Suche in Google Scholar
4h Guillena G. Ramon DJ. Yus M. Tetrahedron: Asymmetry 2007, 18: 693

Suche in Google Scholar
4i Enders D. Narine AA. J. Org. Chem. 2008, 73: 7857

Suche in Google Scholar
For recent examples, see:
5a Manzano R. Andrés JM. Muruzábal MD. Pedrosa R. Adv. Synth. Catal. 2010, 352: 3364

Suche in Google Scholar
5b Imashiro R. Uehara H. Barbas CF. Org. Lett. 2010, 12: 5250

Suche in Google Scholar
5c Urushima T. Sakamoto D. Ishikawa H. Hayashi Y. Org. Lett. 2010, 12: 4588

Suche in Google Scholar
5d Ozeki M. Ochi S. Hayama N. Hosoi S. Kajimoto T. Node M. J. Org. Chem. 2010, 75: 4201

Suche in Google Scholar
5e Liao Y.-H. Chen W.-B. Wu Z.-J. Du X.-L. Cun L.-F. Zhang X.-M. Yuan W.-C. Adv. Synth. Catal. 2010, 352: 827

Suche in Google Scholar
5f Nodes WJ. Nutt DR. Chippindale AM. Cobb AJA. J. Am. Chem. Soc. 2009, 131: 16016

Suche in Google Scholar
5g Zhao G.-L. Vesely J. Rios R. Ibrahem I. Sundén H. Córdova A. Adv. Synth. Catal. 2008, 350: 237

Suche in Google Scholar
5h Ibrahem I. Zhao G.-L. Rios R. Vesely J. Sundén H. Dziedzic P. Córdova A. Chem. Eur. J. 2008, 14: 7867

Suche in Google Scholar
5i Nair V. Babu BP. Vellalath S. Varghese V. Raveendran AE. Suresh E. Org. Lett. 2009, 11: 2507

Suche in Google Scholar
5j Zhu D. Lu M. Dai L. Zhong G. Angew. Chem. Int. Ed. 2009, 48: 6089

Suche in Google Scholar
5k Ishikawa H. Suzuki T. Hayashi Y. Angew. Chem. Int. Ed. 2009, 48: 1304

Suche in Google Scholar
5l Simmons B. Walji AM. MacMillan DWC. Angew. Chem. Int. Ed. 2009, 48: 4349

Suche in Google Scholar
5m McGarraugh PG. Brenner SE. Org. Lett. 2009, 11: 5654

Suche in Google Scholar
5n Bertelsen S. Jøhansen RL. Jørgensen KA. Chem. Commun. 2008, 3016
5o
See ref. 4e.
5p Reyes E. Jiang H. Milelli A. Elsner P. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 9202

Suche in Google Scholar
Recent reviews of domino reactions see:
6a Ramon DJ. Yus M. Angew. Chem. Int. Ed. 2005, 44: 1602

Suche in Google Scholar
6b Guo H. Ma J. Angew. Chem. Int. Ed. 2006, 45: 354

Suche in Google Scholar
6c Pellissier H. Tetrahedron 2006, 62: 2143

Suche in Google Scholar
6d Nicolaou KC. Edmonds DJ. Bulger PG. Angew. Chem. Int. Ed. 2006, 45: 7134

Suche in Google Scholar
6e
Ref. 3a.
6f Enders D. Grondal C. Hüttl MRM. Angew. Chem. Int. Ed. 2007, 46: 1570

Suche in Google Scholar
6g Chapman CJ. Frost CG. Synthesis 2007, 1
6h Pellissier H. Tetrahedron 2006, 62: 1619

Suche in Google Scholar
7 For review of double Michael reactions see: Ihara M. Fukumoto K. Angew. Chem. Int. Ed. 1993, 32: 1010

Suche in Google Scholar
For recent examples, see:
8a Tan B. Shi Z. Chua PJ. Zhong G. Org. Lett. 2008, 10: 3425

Suche in Google Scholar
8b Hao L. Zu L. Xie H. Wang J. Jiang W. Wang W. Org. Lett. 2007, 9: 1833

Suche in Google Scholar
8c Ma A. Ma D. Org. Lett. 2010, 12: 3634

Suche in Google Scholar
8d Liu S.-W. Hsu H.-C. Chang C.-H. Tsai H.-HG. Hou D.-R. Eur. J. Org. Chem. 2010, 4771
8e Mendoza A. Pardo P. Rodríguez F. Fañanás FJ. Chem. Eur. J. 2010, 16: 9758

Suche in Google Scholar
8f Xie FC. Chen H. Hu YH. Org. Lett. 2010, 12: 3086

Suche in Google Scholar
8g Sriramurthy V. Kwon O. Org. Lett. 2010, 12: 1084

Suche in Google Scholar
8h Tan J. Xu X. Zhang L. Li Y. Liu Q. Angew. Chem. Int. Ed. 2009, 48: 2868

Suche in Google Scholar
For reviews:
9a Marco-Contelles J. Molina MY. Anjum S. Chem. Rev. 2004, 104: 2857

Suche in Google Scholar
9b Schultz AG. Acc. Chem. Res. 1990, 23: 207

Suche in Google Scholar
For our recent efforts in exploring new organocatalytic annulations, see:
10a Hong B.-C. Nimje RY. Lin C.-W. Liao J.-H. Org. Lett. 2011, 13: 1278

Suche in Google Scholar
10b Hong B.-C. Dange NS. Hsu C.-S. Liao J.-H. Lee G.-H. Org. Lett. 2011, 13: 1338

Suche in Google Scholar
10c Hong B.-C. Kotame P. Liao J.-H. Org. Biomol. Chem. 2011, 9: 382

Suche in Google Scholar
10d Hong B.-C. Dange NS. Hsu C.-S. Liao J.-H. Org. Lett. 2010, 12: 4812

Suche in Google Scholar
10e Hong B.-C. Kotame P. Tsai C.-W. Liao J.-H. Org. Lett. 2010, 12: 776

Suche in Google Scholar
10f Hong B.-C. Jan R.-H. Tsai C.-W. Nimje RY. Liao J.-H. Lee G.-H. Org. Lett. 2009, 11: 5246

Suche in Google Scholar
10g Hong B.-C. Nimje RY. Liao J.-H. Org. Biomol. Chem. 2009, 7: 3095

Suche in Google Scholar
10h Kotame P. Hong B.-C. Liao J.-H. Tetrahedron Lett. 2009, 50: 704 ; and references cited therein

Suche in Google Scholar
11a Paras NA. MacMillan DWC. J. Am. Chem. Soc. 2001, 123: 4370

Suche in Google Scholar
11b Hong B.-C. Nimje RY. Sadani AA. Liao J.-H. Org. Lett. 2008, 10: 2345

Suche in Google Scholar
11c Bencivenni G. Mazzanti A. Giannichi B. Pesciaioli F. Bartoli G. Melchiorre P. Wu L.-Y. Song M.-P. Angew. Chem. Int. Ed. 2009, 48: 7200

Suche in Google Scholar
11d Penon O. Carlone A. Mazzanti A. Locatelli M. Sambri L. Bartoli G. Melchiorre P. Penon O. Chem. Eur. J. 2008, 14: 4788

Suche in Google Scholar
11e Jiang K. Jia Z.-J. Chen S. Wu L. Chen Y.-C. Chem. Eur. J. 2010, 16: 2852

Suche in Google Scholar
12a Tite T. Lallemand M.-C. Poupon E. Kunesch N. Tillequin F. Gravier-Pelletier C. Merrerb YL. Husson H.-P. Bioorg. Med. Chem. 2004, 12: 5091

Suche in Google Scholar
12b Xiao D. Wang C. Palani A. Reichard G. Aslanian R. Shih N.-Y. Buevich A. Tetrahedron: Asymmetry 2006, 17: 2596

Suche in Google Scholar
12c Roulland E. Chiaronia A. Hussonb H.-P. Tetrahedron Lett. 2005, 46: 4065

Suche in Google Scholar
For recent examples, see:
13a Airiau E. Girard N. Mann A. Salvadori J. Taddei M. Org. Lett. 2009, 11: 5314

Suche in Google Scholar
13b Agami C. Couty F. Evano G. Eur. J. Org. Chem. 2002, 29
13c Cutri S. Diez A. Bonin M. Micouin L. Husson H.-P. Org. Lett. 2005, 7: 1911

Suche in Google Scholar
13d Roulland E. Cecchin F. Husson H.-P. J. Org. Chem. 2005, 70: 4474

Suche in Google Scholar
13e Poupon E. Francüois D. Kunesch N. Husson H.-P.
J. Org. Chem. 2004, 69: 3836

Suche in Google Scholar
13f Francois D. Poupon E. Kunesch N. Husson H.-P. Eur. J. Org. Chem. 2004, 4823
13g Laurent P. Braekman J.-C. Daloze D. Eur. J. Org. Chem. 2000, 2057
13h Amat M. Elias V. Llor N. Subrizi F. Bosch J. Molins E. Eur. J. Org. Chem. 2010, 4017
13i Amat M. Gomez-Esque A. Escolano C. Santos MMM. Bosch J. Molins E. J. Org. Chem. 2009, 74: 1205

Suche in Google Scholar
13j Amat M. Santos MMM. Gomez AM. Jokic D. Molins E. Bosch J. Org. Lett. 2007, 9: 2907

Suche in Google Scholar
13k Amat M. Santos MMM. Bassas O. Llor N. Escolano C. Gomez-Esque A. Molins E. Allin SM. McKee V. Bosch J. J. Org. Chem. 2007, 72: 5193

Suche in Google Scholar
13l Amat M. Bassas O. Llor N. Canto M. Perez M. Molins E. Bosch J. Chem. Eur. J. 2006, 12: 7872

Suche in Google Scholar
13m Amat M. Perez M. Minaglia AT. Casamitjana N. Bosch J. Org. Lett. 2005, 7: 3653

Suche in Google Scholar
13n Bassas O. Llor N. Santos MMM. Griera R. Molins E. Amat M. Bosch J. Org. Lett. 2005, 7: 2817

Suche in Google Scholar
13o Amat M. Bassas O. Pericas MA. Pasto M. Bosch J. Chem. Commun. 2005, 1327
13p Amat M. Canto M. Llor N. Ponzo V. Perez M. Bosch J. Angew. Chem. Int. Ed. 2002, 41: 335

Suche in Google Scholar
15 For a similar reaction with dynamic kinetic resolution, see: Amat M. Pérez M. Minaglia AT. Peretto B. Bosch J. Tetrahedron 2007, 63: 5839 ; and references cited therein

Crossref Suche in Google Scholar
dr = 5:1. For similar examples, see:
16a
Ref. 3e.
16b Enders D. Hüttl MRM. Raabe G. Bats JW. Adv. Synth. Catal. 2008, 350: 267

Suche in Google Scholar
16c Enders D. Hüttl MRM. Runsink J. Raabe G. Wendt B. Angew. Chem. Int. Ed. 2007, 46: 467

Suche in Google Scholar
16d Enders D. Hüttl MRM. Grondal C. Raabe G. Nature 2006, 441: 861

Suche in Google Scholar
16e Varela MC. Dixon SM. Lam KS. Schore NE. Tetrahedron 2008, 64: 10087

Suche in Google Scholar

14

The reaction with 1 equiv of dl-Ser-OMeHCl for 8 h resulted in ˜50% conversion of 3a.

17

CCDC-815738 contains the supplementary crystallographic data for (-)-3e, radiation type: CuKα. CCDC-815739 contains the supplementary crystallographic data for (-)-3e, radiation type: MoKα. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.