Enantioselective allene/enone photocycloadditions: The use of an inexpensive optically active 1,3-disubstituted allene

Tetrahedron

Volumn 53, Issue 48, 1997, Pages 16253-16276

  Shepard, Mary S ^a   Carreira, Erick M ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE;

CONFERENCE PAPER; OPTICAL ROTATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030730768     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01013-2     Document Type: Conference Paper

References (36)

1. (a) Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
2. (b) Crimmins, M. T.; Reinhold, T. L. Org. React.; Wiley: New York, 1993; Vol. 44, 297.
3. (c) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003.
4. (d) Schreiber, S. L. Science 1985, 227, 857.
5. (e) Wiesner, K. Tetrahedron 1975, 31, 1655.
6. (a) Carreira, E. M.; Hastings, C. A.; Shepard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc. 1994, 116, 6622.
7. (b) Shepard, M. S.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 2597.
8. (a) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
9. (b) Carreira, E. M.; Singer, R. A. Drug Discovery Today 1996, 1, 145.
10. (a) Nightingale, D.; Wadsworth, F. T. J. Am. Chem. Soc. 1947, 69, 1181.
11. (b) Hauptmann, H.; Mader, M. Synthesis 1978, 307.
12. Midland, M. M.; Tramontano, A.; Zderic, S. A. J. Am. Chem. Soc. 1977, 99, 5211.
13. Yamaguchi, S.; Mosher, H. S.; Pohland, A. J. Am. Chem. Soc. 1972, 94, 9254.
14. Brinkmeyer, R. S.; Kapoor, V. M. J. Am. Chem. Soc. 1977, 99, 8339.
15. Midland, M. M.; Kazubski, A.; Woodling, R. E. J. Org. Chem. 1991, 56, 1068.
16. Nishizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett. 1981, 22, 247.
17. Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16.
18. (a) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938.
19. (b) Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Vilarrasa, J. J. Org. Chem. 1996, 61, 9021.
20. Schmidt, B.; Seebach, D. Angew. Chem. 1991, 103, 1383; Angew. Chem., Int. Ed. Engl. 1991, 30, 1321.
21. Schmidt, B.; Seebach, D. Angew. Chem. 1991, 103, 1383; Angew. Chem., Int. Ed. Engl. 1991, 30, 1321.
22. Corey, E. J.; Cimprich, K. A. J. Am. Chem. Soc. 1994, 116, 3151.
23. Kobayashi, S.; Furuya, M.; Ohtsubo, A.; Mukaiyama, T. Tetrahedron: Asymmetry 1991, 2, 635.
24. The addition of 2-methoxypropene to alkynyl aldehydes to give acetone-aldol adducts has recently been reported, see: Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649.
25. We have recently reported a procedure involving in situ preparation of the catalyst for the enantioselective aldol addition reaction which considerably simplifies the experimental procedure on preparative scale, see: Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927.
26. For an alternative synthesis of optically active propargyl alcohols as precursors to chiral allenes, see: 2b.
27. (a) Myers, A. G.; Finney, N. S.; Kuo, E. Y. Tetrahedron Lett. 1989, 30, 5747.
28. For more recent developments in this area, see: (b) Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
29. For an elegant application of photocycloaddition followed by retromannich fragmentation sequence, see: Winkler, J. D.; Hershberger, P. M.; Springer, J. P. Tetrahedron Lett. 1986, 27, 5177.
30. The absolute stereochemistry of the adducts is presumed to parallel that previously reported for the tert-butyl-substituted allenes, for which X-ray crystallographic analysis of a derivative was possible (ref 2a). To date, we have been unable to obtain crystalline material of 21-28 and their derivatives.
31. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
32. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
33. Baraldi, P. G.; Simoni, D.; Manfredini, S. Synthesis 1983, 902.
34. Shaw, K. N. F.; McMillan, A.; Armstrong, M. D. J. Org. Chem. 1956, 21, 601.
35. Ivanov, I. C.; Karagiosov, S. K.; Manolov, I. Arch. Pharm. (Weinheim) 1991, 324, 61.
36. Schell, F. M.; Williams, P. R., Jr. Synth. Commun. 1982, 12, 755.