Stereoselective Formation of Fully Substituted Ketone Enolates

Citation:

Haimov, E. ; Nairoukh, Z. ; Shterenberg, A. ; Berkovitz, T. ; Jamison, T. F. ; Marek, I. . Stereoselective Formation Of Fully Substituted Ketone Enolates. Angew. Chem. Int. Ed. 2016, 55, 5517 – 5520 2016.

Date Published:

2016

Abstract:

Abstract The application of stereochemically defined acyclic fully substituted enolates of ketones to the enantioselective synthesis of quaternary carbon stereocenters would be highly valuable. Herein, we describe an approach leading to the formation of several new stereogenic centers through a combined metalation?addition of a carbonyl?carbamoyl transfer to reveal in?situ stereodefined α,α-disubstituted enolates of ketone as a single stereoisomer. This approach could produce a series of aldol and Mannich products from enol carbamate with excellent diastereomeric ratios.

Notes:

https://doi.org/10.1002/anie.201601883

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Last updated on 05/19/2021