A versatile approach to N-Boc-statine and N-Boc-norstatine based on the reduction of 1-trialkylsilyl acetylenic ketones. Strong remote effect of the C(1) substituent on the stereoselectivity

Authors
Alemany, C Bach, J Farras, J Garcia, J
Citation
C. Alemany et al., A versatile approach to N-Boc-statine and N-Boc-norstatine based on the reduction of 1-trialkylsilyl acetylenic ketones. Strong remote effect of the C(1) substituent on the stereoselectivity, ORG LETT, 1(11), 1999, pp. 1831-1834
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
11
Year of publication
1999
Pages
1831 - 1834
Database
ISI
SICI code
1523-7060(199912)1:11<1831:AVATNA>2.0.ZU;2-#
Abstract
[GRAPHICS] An efficient, unified approach to chiral, protected beta-hydroxy gamma-amin o and alpha-hydroxy beta-amino acids derived from Boc-L-leucine has been ac complished on the basis of the oxazaborolidine-controlled, stereoselective reduction of 1-trialkylsilyl acetylenic ketones; stereoselectivity in the r eduction step has shown strong dependence upon C(1) substitution.