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Updated: Sep 6, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Accessing Diverse Cross-Benzoin and α-Siloxy Ketone Products via Acyl Substitution Chemistry
Chloe N Larcombe1, Lara R Malins1
1Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia.
Abstract:
An approach to diverse cross-benzoin and α-siloxy ketone products which leverages a simple yet underutilized C-C bond disconnection strategy is reported. Acyl substitution of readily accessible α-siloxy Weinreb amides with organolithium compounds enables access to a broad scope of aryl, heteroaryl, alkyl, alkenyl, and alkynyl derivatives. Enantiopure benzoins can be accessed via a chiral pool approach, and the utility of accessible cross-benzoins and α-siloxy ketones is highlighted in a suite of downstream synthetic applications.
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