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ChemInform Abstract: Unusual Preference for Ketone and Reversal of Chemoselectivity in Lewis Acid-Catalyzed Aldol Reaction of Ketene Silyl Acetal.

✍ Scribed by Jian-xie Chen; Katsumasa Sakamoto; Akihiro Orita; Junzo Otera

Publisher: John Wiley and Sons
Year: 2010
Weight: 37 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199923047

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✦ Synopsis

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 exemplified by intramolecular competition experiments with keto aldehydes or keto acetals.

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