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

Add time:07/27/2019    Source:sciencedirect.com

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 desilylation of these esters occurs with complete retention of configuration yielding the corresponding (2R,3S)-2,3-dihydroxy-2-methyl-alkanoic acids.

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