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Lewis acid promoted aldol additions of α-thiosilylketeneacetals to α-alkoxy aldehydes: diastereoselective synthesis of syn-α-methylene-β-hydroxy-∂-alkoxy esters.

✍ Scribed by Anna Bernardi; Silvia Cardani; Cesare Gennari; Giovanni Poli; Carlo Scolastico

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 190 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)99039-7

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✦ Synopsis

MgBr mediated addition of to A'and Methyl &-methylthio propionate silylketene acetal o(,p-alkoxy aldehydes is highly 3,4 syn-selective (18:l). syn-d-methylene$-hydroxy-s-alkoxy esters (6) and (8) are synthesized. We recently reported that I butyIP-dimethylamino propionate, a synthetic equivalent of t-butyl acrylate, -readily reacts with d-alkoxy aldehydes to give anti-A-methylene-F--hydroxy-l-alkoxy esters (1) (Felkin-Anh products) with high selectivity.' The double bond of these compounds and of the corresponding &-lactones was further elaborated and some branched sugars were obtained in the ribo and arabino series. ' As a development of this project,we became interested in the St&-eoselective synthesis of

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