Stereoselective Formation of Fully Substituted Ketone Enolates

Elvira Haimov, Zackaria Nairoukh, Alexander Shterenberg, Tiran Berkovitz, Timothy F. Jamison, Ilan Marek*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

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.

Original languageAmerican English
Pages (from-to)5517-5520
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number18
DOIs
StatePublished - 25 Apr 2016
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

  • carbamoyl transfer
  • enol carbamates
  • enolates
  • ketones
  • quaternary carbon stereocenters

Fingerprint

Dive into the research topics of 'Stereoselective Formation of Fully Substituted Ketone Enolates'. Together they form a unique fingerprint.

Cite this