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Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones

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Title
Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones
Author
Bae, Han YongList, Benjamin
Keywords
aldol reaction;  Lewis acids;  Mukaiyama aldol reaction;  parts-per-million;  silyl ketene acetal;  tertiary aldols
Issue Date
201809
Publisher
WILEY-V C H VERLAG GMBH
Citation
CHEMISTRY-A EUROPEAN JOURNAL, v.24, no.52, pp.13767 - 13772
Abstract
The Mukaiyama aldol reaction is a widely applied carbon-carbon bond forming reaction. However, despite numerous well-established methods using aldehydes as acceptors, only few examples exist with ketones. Here we report a highly practical catalytic approach to this transformation, namely, the triflimide catalyzed Mukaiyama aldol reaction of silyl ketene acetals with ketones. This method exhibits a broad substrate scope, is very rapid, tolerates functionalized substrates, and requires only parts-per-million catalyst loadings with preparative scale reactions up to hundreds of grams in excellent purity (>99%).
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DOI
http://dx.doi.org/10.1002/chem.201803142
ISSN
0947-6539
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