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High diastereoselectivity in lewis acid mediated aldol condensations using thioester silyl ketene acetals.

โœ Scribed by Cesare Gennari; Anna Bernardi; Silvia Cardani; Carlo Scolastico


Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
248 KB
Volume
26
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


BF30Et2 mediated aldol condensations of thioester silyl ketene acetals are stereoconvergent, and exhibit high internal (anti) and relative (Cram) diastereoselectivity.


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Ketene silyl acetals such as (II) and (IV) are added in the presence of various Lewis acids (e.g. (C 6 F 5 ) 2 SnBr 2 ) to ketones with a extremely high level of chemoselectivity in competition with aldehydes or acetales (with exception of benzaldehyde). The generality of ketone preference is also e