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Lewis acid mediated 1,2-asymmetric lk-induction to α-alkoxyaldehyde: synthesis of α-nonsubstituted β, γ-syn-dihydroxyketone and ester

✍ Scribed by Jun-ichi Uenishi; Hideo Tomozane; Masatoshi Yamato

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 227 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)98666-0

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✦ Synopsis

Lewis acid mediated reactions of methylthio substituted silyl enolate or ketene silyl acetal to a-alkoxyaldehyde give syn diols. A novel stereocontrolled synthesis of a-nonsubstituted B,y-dihydroxyketone and ester is described.

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## Abstract Starting substrates, enantiopure spiranic or 3‐substituted 3‐alkoxy‐4‐oxoazetidine‐2‐carbaldehydes, were prepared from (__R__)‐2,3‐__O__‐isopropylideneglyceraldehyde derived azetidine‐2,3‐diones by sequential Barbier‐type addition reactions followed by hydroxy functionalization and alde