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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 9
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Original Articles

Enantioselective Silicon-Mediated Synthesis of Glyceraldehyde Derivatives from Propargyl Alcohol

Piotr Raubo Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224, Warsaw, Poland
&
Jerzy Wicha Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224, Warsaw, Poland
Pages 1273-1288 | Received 06 Nov 1992, Published online: 24 Sep 2006
 
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Abstract

Asymmetric epoxidation of 3-(trimethylsilyl)allyl alcohol affords epoxysilane 5 of high optical purity. Silica gel-catalyzed addition of benzenethiol to epoxide 5 affords sulfide 8 which was transformed into (2S)-2,3-O-isopropylideneglyceraldehyde 2 and the glyceraldehyde derivative 3.

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