A Novel Synthesis of syn and anti β-Hydroxy Dithioacetals, Masked Cross-Aldols between Aldehydes

Ketene dithioacetals readily reacted with aldehydes in the presence of a Lewis acid such as BF3·OEt2 or TMSOTf to generate the cationic adducts, which in turn reacted with NaAlH2(OCH2CH2OCH3)2, leading to the corresponding β-hydroxy dithioacetals, masked cross-aldols between aldehydes. Each diastere...

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Bibliographic Details
Published in:Chemistry letters 2004-08, Vol.33 (8), p.1032-1033
Main Authors: Saitoh, Terunobu, Jimbo, Naohisa, Ichikawa, Junji
Format: Article
Language:English
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Summary:Ketene dithioacetals readily reacted with aldehydes in the presence of a Lewis acid such as BF3·OEt2 or TMSOTf to generate the cationic adducts, which in turn reacted with NaAlH2(OCH2CH2OCH3)2, leading to the corresponding β-hydroxy dithioacetals, masked cross-aldols between aldehydes. Each diastereomer was selectively obtained by choosing the appropriate Lewis acid and substituents on the sulfur atoms of the ketene dithioacetals.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2004.1032