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

doi:10.1039/c6sc03036j

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 journal › Article › peer-review

20 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 language	American English
Pages (from-to)	627-630
Number of pages	4
Journal	Chemical Science
Volume	8
Issue number	1
DOIs	https://doi.org/10.1039/c6sc03036j
State	Published - 2016
Externally published	Yes

Bibliographical note

Funding Information:
This research was supported by the European Research Council under the European Community's Seventh Framework Program (ERC grant agreement no. 338912) and by the Israel Science Foundation administrated by the Israel Academy of Sciences and Humanities (140/12). I. M. is holder of the Sir Michael and Lady Sobell Academic Chair.

Publisher Copyright:
© The Royal Society of Chemistry

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

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.",

author = "Zackaria Nairoukh and Kumar, {Gunda G.K.S.Narayana} and Yury Minko and Ilan Marek",

note = "Funding Information: This research was supported by the European Research Council under the European Community's Seventh Framework Program (ERC grant agreement no. 338912) and by the Israel Science Foundation administrated by the Israel Academy of Sciences and Humanities (140/12). I. M. is holder of the Sir Michael and Lady Sobell Academic Chair. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry",

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doi = "10.1039/c6sc03036j",

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AU - Nairoukh, Zackaria

AU - Kumar, Gunda G.K.S.Narayana

AU - Minko, Yury

AU - Marek, Ilan

N1 - Funding Information: This research was supported by the European Research Council under the European Community's Seventh Framework Program (ERC grant agreement no. 338912) and by the Israel Science Foundation administrated by the Israel Academy of Sciences and Humanities (140/12). I. M. is holder of the Sir Michael and Lady Sobell Academic Chair. Publisher Copyright: © The Royal Society of Chemistry

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

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DO - 10.1039/c6sc03036j

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JF - Chemical Science

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ER -

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

Abstract

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