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Stereoselective Formation of Fully Substituted Ketone Enolates |
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| Authors: | Elvira Haimov Dr Zackaria Nairoukh Dr Alexander Shterenberg Tiran Berkovitz Prof Dr Timothy F Jamison Prof Dr Ilan Marek |
| Institution: | 1. The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa, Israel;2. Massachusetts Institute of Technology, Department of Chemistry, Cambridge, MA, USA |
| 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. |
| Keywords: | carbamoyl transfer enol carbamates enolates ketones quaternary carbon stereocenters |