Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres

Zackaria Nairoukh, Gunda G.K.S.Narayana Kumar, Yury Minko, Ilan Marek*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

A sequence of regio- and stereoselective carbometalation followed by oxidation of ynamides leads to stereodefined fully substituted enolates that subsequently react with various functionalized allyl bromide reagents to provide the expected products possessing an enantiomerically pure quaternary carbon stereocentre in the α-position to the carbonyl group in excellent yields and enantiomeric ratios after cleavage of the oxazolidinone moiety. Three new bonds are formed in a single-pot operation.

Original languageAmerican English
Pages (from-to)627-630
Number of pages4
JournalChemical Science
Volume8
Issue number1
DOIs
StatePublished - 2016
Externally publishedYes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry

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