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- Title
Mixed Monosilyl Acetals and Catalyst-Dependent Chemoselective Mukaiyama Aldol Reactions.
- Authors
Kim, Sun Min; Yang, Hye Sung; Eum, Heesung; Ha, Hyun ‐ Joon; Yang, Jung Woon
- Abstract
We report a direct, simple, and straightforward approach for the construction of a mixed monosilyl acetal as a new and synthetically valuable functional group by mixing an aldehyde, sodium tert-butoxide, and trimethylsilyl azide. We also demonstrate a catalyst-dependent chemoselective reaction between mixed monosilyl acetals and silyl ketene acetals through Mukaiyama aldol reactions to give different structures of O-protected β-hydroxy esters in excellent yields with high chemoselectivities. This study provided the existence of an oxonium ion intermediate and of its kinetically controlled reaction with the pre-equilibrated silyl enol ether obtained from ( E)- and ( Z)-isomerization.
- Subjects
ACETAL resins; ALDOLS; CHEMICAL reactions; CHEMICAL structure; MIXING
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 65, p16432
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201704456