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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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Bae,  Han Yong
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Bae, H. Y., & List, B. (2018). Triflimide: An Overlooked High‐Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones. Chemistry – A European Journal, 24(52), 13767-13772. doi:10.1002/chem.201803142.


Cite as: http://hdl.handle.net/21.11116/0000-0002-57A4-3
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 %).