Catalytic diastereoselective reduction of α,β-epoxy and α,β-aziridinyl ynones

Organic Letters

Volumn 14, Issue 2, 2012, Pages 516-519

  Druais, Valérie ^a   Meyer, Christophe ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AZIRIDINE; AZIRIDINE DERIVATIVE; EPOXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ALCOHOLS; AZIRIDINES; CATALYSIS; EPOXY COMPOUNDS; HYDROGENATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84856103021     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol203114a     Document Type: Article

References (44)

1. Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1995.
2. For a recent review, see: Trost, B. M.; Weiss, A. H. Adv. Synth. Catal. 2009, 351, 963-983
3. Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938-10939
4. Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 1996, 61, 3214-3217
5. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739
6. Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667-3670
7. Fujii, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736
8. Shin, Y.; Fournier, J.-H.; Fukui, Y.; Brückner, A. M.; Curran, D. P. Angew. Chem., Int. Ed. 2004, 43, 4634-4637
9. Maki, K.; Motoki, R.; Fujii, K.; Kanai, M.; Kobayashi, T.; Tamura, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 17111-17117
10. Trost, B. M.; Frederiksen, M. U.; Papillon, J. P. N; Harrington, P. E.; Shin, S.; Shireman, B. T. J. Am. Chem. Soc. 2005, 127, 3666-3667
11. Fukui, Y.; Brückner, A. M.; Shin, Y.; Balachandran, R.; Day, B. W.; Curran, D. P. Org. Lett. 2006, 8, 301-304
12. Ferrié, L.; Reymond, S.; Capdevielle, P.; Cossy, J. Org. Lett. 2007, 9, 2461-2464
13. Mandel, A. L.; Bellosta, V.; Curran, D. P.; Cossy, J. Org. Lett. 2009, 11, 3282-3285
14. Marshall, J. A.; Bourbeau, M. P. Org. Lett. 2003, 5, 3197-3199
15. Marshall, J. A.; Ellis, K. Tetrahedron Lett. 2004, 45, 1351-1353
16. Cantagrel, G.; Meyer, C.; Cossy, J. Synlett 2007, 2983-2986
17. Barbazanges, M.; Meyer, C.; Cossy, J. Org. Lett. 2008, 10, 4489-4492
18. Handa, M.; Scheidt, K. A.; Bossart, M.; Zheng, N.; Roush, W. R. J. Org. Chem. 2008, 73, 1031-1035
19. Hesse, O. J. Prakt. Chem. 1900, 62, 430-480
20. Huneck, S.; Schreiber, K.; Steglich, W. Tetrahedron 1973, 29, 3687-3693
21. Pal, S. Tetrahedron 2006, 62, 3171-3200
22. Lewis, M. D.; Menes, R. Tetrahedron Lett. 1987, 28, 5129-5132
23. Wright, J. J.; Puar, M. S.; Pramanik, B.; Fishman, A. J. Chem. Soc., Chem. Commun. 1988, 413-414
24. Lewis, M. D.; Duffy, J. P.; Heck, J. V.; Menes, R. Tetrahedron Lett. 1988, 29, 2279-2282
25. Yadav, J. S.; Rajagopal, D. Tetrahedron Lett. 1990, 31, 5077-5080
26. Nakao, Y.; Maki, T.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. Tetrahedron 2000, 56, 8977-8987
27. Mohapatra, D. K.; Bhattasali, D.; Gurjar, M. K.; Khan, M. I.; Shashidhara, K. S. Eur. J. Org. Chem. 2008, 6213-6224
28. For a review on the ring opening of α,β-epoxy alcohols, see: Behrens, C. H.; Sharpless, K. B. Aldrichimica Acta 1983, 16, 65-79
29. Roush, W. R.; Brown, R. J.; DiMare, M. J. Org. Chem. 1983, 48, 5083-5093
30. Roush, W. R.; Straub, J. A.; VanNieuwenhze, M. S. J. Org. Chem. 1991, 56, 1636-1648
31. For a recent contribution, see: Mukerjee, P.; Abid, M.; Schroeder, F. C. Org. Lett. 2010, 12, 3986-3989
32. Marson, C. M.; Edaan, E.; Morrell, J. M.; Coles, S. J.; Hursthouse, M. B.; Davies, D. T. Chem. Commun. 2007, 2494-2496
33. Strong match/mismatch pairing has been previously noted during the CBS reduction of an ynone possessing an adjacent acetonide derived from an anti-1,2 -diol; see: RajanBabu, T. V.; Nugent, W. A.; Taber, D. F.; Fagan, P. J. J. Am. Chem. Soc. 1988, 110, 7128-7135
34. Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226-2227
35. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191-1224
36. Yamakawa, M.; Yamada, I.; Noyori, R. Angew. Chem., Int. Ed. 2001, 40, 2818-2821
37. Taniguchi, M.; Fujii, H.; Oshima, K.; Utimoto, K. Tetrahedron 1995, 51, 679-686
38. Li, K.; Hamann, L. G.; Koreeda, M. Tetrahedron Lett. 1992, 33, 6569-6570
39. Fujii, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 967-970
40. Nakata, T.; Tanaka, T.; Oishi, T. Tetrahedron Lett. 1981, 22, 4723-4726
41. For a review on α,β-epoxy ketones, see: Lauret, C. Tetrahedron: Asymmetry 2001, 12, 2359-2383
42. Li, J.; Park, S.; Miller, R. L.; Lee, D. Org. Lett. 2009, 11, 571-574
43. Yun, J. M.; Sim, H. S.; Lee, W. K.; Ha, H.-J. J. Org. Chem. 2003, 68, 7675-7680
44. Singh, A.; Kim, B.; Lee, W. K.; Ha, H.-J. Org. Biomol. Chem. 2011, 9, 1372-1380