Enantiospecific generation of anti-aldol adducts via conjugate addition to 5-methylene-1,3-dioxan-4-ones

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2043-2046

  Piber, Michael ^a   Leahy, James W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 METHYLENE 1,3 DIOXAN 4 ONE DERIVATIVE; ALKENE; DIOXANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CONJUGATION; ENANTIOMER; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032499148     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00183-X     Document Type: Article

References (19)

1. 1. For a review of recent trends in organic synthesis, see: Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press, Oxford, 1991.
2. 2. Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317.
3. 3. For recent reviews on the Baylis-Hillman reaction, see: a) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
4. b) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
5. 4. For excellent reviews of the aldol reaction, see: a) Heathcock, C. H. in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 3, pp 112-212.
6. b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
7. c) Heathcock, C. H. in Comprehensive Organic Synthesis; Trost B. M. and Fleming, I., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 133-238.
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9. 5. Recently, an efficient anti aldol process has been reported. See: Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586.
10. 6. For a recent review, see: Organocopper Reagents, Taylor, R. J. K., Ed.; Oxford University Press, UK, 1994.
11. 7. For a similar study, see: Amberg, W.; Seebach, D. Chem. Ber. 1990, 123, 2413.
12. 13C (75 MHz) NMR spectra. Configuration about the newly formed stereocenters was determined via analysis of coupling constants and the pertinent nuclear Overhauser enhancements.
13. 9. Amberg, W.; Seebach, D. Chem. Ber. 1990, 123, 2429.
14. 10. See Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237 and references cited within.
15. 11. Tomioka, K.; Kawasaki, H.; Yasuda, K.; Koga, K. J. Am. Chem. Soc. 1988, 110, 3597.
16. 12. Seebach has reported the use of a Schwesinger P4 base for the alkylation of similar dioxanones (Pietzonka, T.; Seebach, D. Chem. Ber. 1991, 124, 1837) and work is underway to examine this possibility with the corresponding products derived from the asymmetric Baylis-Hillman reaction.
17. 13. For a similar study, see: Bulliard, M.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1991, 74, 1600.
18. 15 In this system, such a geometry would result in all of the substituents adopting an equatorial orientation. We are grateful to the referee for making this alternative suggestion. (equation presented)
19. 15. Lomas, J. S.; Fain, D.; Briand, S. J. Org. Chem. 1990, 55, 1052.