Synthesis and desilylation of (2R, 3S)-α-methyl-α-silyl-α, β-2, 3-dihydroxycarboxylic methyl esters

A Battaglia, E Baldelli, G Barbaro, P Giorgianni…

Index: Battaglia, Arturo; Baldelli, Eleonora; Barbaro, Gaetano; Giorgianni, Patrizia; Guerrini, Andrea; Monari, Magda; Selva, Simona Tetrahedron Asymmetry, 2002 ,  vol. 13,  # 16  p. 1825 - 1832

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Citation Number: 9

Abstract

Addition reactions of the chiral lithium (2S)-enolates of the (2S, 5S)-2-tert-butyl-5-methyl-[1, 3] dioxolan-4-one and (2S, 5S)-2-tert-butyl-2, 5-dimethyl-[1, 3] dioxolan-4-one with linear aliphatic acylsilanes yield the corresponding (2S, 5R, 1′ R)-1′-trimethylsilyl-dioxolanone alcohols. Sodium methoxide-induced removal of the acetal center at C-2 affords the corresponding methyl (2R, 3R)-2, 3-dihydroxy-2-methyl-3-trimethylsilyl alkanoates. The ...