Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones
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- Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones
- Bae, Han Yong; List, Benjamin
- aldol reaction; Lewis acids; Mukaiyama aldol reaction; parts-per-million; silyl ketene acetal; tertiary aldols
- Issue Date
- WILEY-V C H VERLAG GMBH
- CHEMISTRY-A EUROPEAN JOURNAL, v.24, no.52, pp.13767 - 13772
- 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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