The mechanistic basis for diastereoselectivity in the Matteson rearrangement

Tetrahedron Asymmetry

Volumn 8, Issue 22, 1997, Pages 3711-3713

  Corey, E J ^a   Barnes Seeman, David ^a   Lee, Thomas W ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBORON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030834792     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00528-4     Document Type: Article

References (13)

1. (a) Matteson, D. S. Acc. Chem. Res. 1988, 21, 294.
2. (b) Matteson, D. S. Chem. Rev. 1989, 89, 1535.
3. (c) Matteson, D. S.; Hurst, G. D. Heteroatom Chem. 1990, 1, 65.
4. (d) Matteson, D. S. in Stereodirected Synthesis with Organoboranes, Springer-Verlag, Berlin, 1995, Chapter 5.
5. (a) Corey, E. J.; Rohde, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Letters 1997, 38, 33.
6. (b) Corey, E. J.; Rohde, J. J. Tetrahedron Letters 1997, 38, 37.
7. (c) Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Letters 1997, 38, 1699.
8. (d) Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Letters 1997, 38.
9. See also for oxazaborolidine-catalyzed reductions, (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
10. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C. P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
11. (c) Corey, E. J.; Helal, C. J. Tetrahedron Letters 1995, 36, 9153.
12. (d) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938.
13. This research was supported by grants from the National Science Foundation and the National Institutes of Health. D.B.-S. and T.W.L. are Graduate Fellows of the National Science Foundation.