Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters

Zackaria Nairoukh, Ilan Marek*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

The regio- and stereoselective formation of stereodefined polysubstituted silyl ketene aminals is easily achieved through selective combined carbometalation-oxidation-silylation reactions. These substrates are ideal candidates for Mukaiyama aldol reactions with aliphatic aldehydes as they give the aldol products with a quaternary carbon stereocenter α to the carbonyl groups in outstanding diastereoselectivities.

Original languageAmerican English
Pages (from-to)14393-14397
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number48
DOIs
StatePublished - 23 Nov 2015
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

  • Mukaiyama reaction
  • aldols
  • one-pot reactions
  • quaternary carbon stereocenters
  • silyl ketene aminals

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