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

• Published in: Tetrahedron: asymmetry Vol. 13; no. 16; pp. 1825 - 1832
• Main Authors: Battaglia, Arturo, Baldelli, Eleonora, Barbaro, Gaetano, Giorgianni, Patrizia, Guerrini, Andrea, Monari, Magda, Selva, Simona
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 27-08-2002
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/S0957-4166(02)00440-8

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