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Synlett 2001; 2001(11): 1772-1776
DOI: 10.1055/s-2001-18107
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Highly Stereoselective α-Alkylations, 1,4-Additions, and One-pot 1,4-Addition/α-Methylations Achieved on 4-O-Acyl and 4-O-Crotonyl Derivatives of Methyl 6-Deoxy-2,3-di-O-(t-butyldimethylsilyl)-α-D-glucopyranoside

Kiichiro Totani* , Shingo Asano, Ken-ichi Takao, Kin-ichi Tadano
  • *Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan; Fax + 81(45)5 66 15 71; E-mail: tadano@applc.keio.ac.jp
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Publication Date:
29 October 2001 (online)

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Benzylation or methylation of the enolate generated from 4-O-propionyl or 4-O-3-phenyl-propionyl derivatives of methyl 6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-α-D-glucopyranoside provided the respective C-alkylated product stereoselectively. The 1,4-additions of a variety of carbon nucleophiles to the corresponding 4-O-crotonyl derivative provided adducts with high and complementary diastereoselection. The one-pot 1,4-additions of a phenyl nucleophile to the 4-O-crotonyl ester followed by the addition of methyl iodide provided vicinally substituted products with high diastereo- and enantioselectivity, from which diastereomeric α-methyl-β-phenylbutanols were obtained in enantioenriched form after reductive removal of the carbohydrate template.

diastereoselectivity - carbohydrates - chiral auxiliaries - Michael-additions - alkylations