The use of phosphinamide N-protecting groups in the diastereoselective reduction of ketones

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2315-2316

  Palmer, Matthew J ^a   Studley, John R ^a   Walsgrove, Tim C ^b   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0031592555     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00302-X     Document Type: Article

References (13)

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3. (c) M. P. Gamble, J. R. Studley and M. Wills, Tetrahedron Lett., 1996, 37, 2853.
4. (d) M. P. Gamble, J. R. Studley and M. Wills, Tetrahedron: Asymmetry. 1996, 7, 3071.
5. 2. (a) G. W. Kenner, G. A. Moore and R. Ramage, Tetrahedron Lett., 1976, 3623.
6. (b) R. Ramage, D. Hopton, M. J. Parrott, G. W. Kenner and G. A. Moore, J. Chem. Soc., Perkin Trans. I, 1984, 1357.
7. (c) R. Ramage, B. Atrash, D. Hopton and M. J. Parrott, J. Chem. Soc., Perkin Trans. I, 1985, 1217.
8. 3. (a) A. G. Myers and T. Yoon, Tetrahedron Lett., 1995, 36, 9429.
9. (b) A. G. Myers, T. Yoon and J. L. Gleason, Tetrahedron Lett., 1995, 36, 4555.
10. (c) A. G. Myers, B. H. Yang and D. J. Kopecky, Tetrahedron Lett., 1996, 37, 3623.
11. (d) A. G. Myers, J. L. Gleason and T. Yoon, J. Am. Chem. Soc., 1995, 117, 8488.
12. (e) A. G. Myers, B. H. Yang, H. Chen and J. L. Gleason, J. Am. Chem. Soc., 1994, 116, 9361.
13. 3b In our hands 4c was formed in 71% yield from the corresponding acid and 4b was formed in 31% overall yield from the t-Boc protected valine (4 processes in two pots).