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Issue 73, 2017
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Asymmetric conjugate addition of alkylzirconium reagents to α,β-unsaturated thioesters: access to fragrances and acyclic stereochemical arrays

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Abstract

Copper-catalyzed asymmetric conjugate addition of alkylzirconium species to α,β-unsaturated thioesters is reported. A variety of functionalized alkyl nucleophiles were introduced with yields around 70% and ee's over 92%. The method was applied to the straightforward syntheses of the commercially important fragrances phenoxanol (both enantiomers 97% ee), and hydroxycitronellal (98% ee). The 1,4-addition products can be converted to enantiomerically enriched linear building blocks bearing a terminal functional group. Formation of further α,β-unsaturated thioesters provides an iterative route for the stereocontrolled synthesis of functionalized acyclic arrays and we demonstrate almost complete catalyst control in the formation of additional stereocentres.

Graphical abstract: Asymmetric conjugate addition of alkylzirconium reagents to α,β-unsaturated thioesters: access to fragrances and acyclic stereochemical arrays

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Supplementary files

Article information


Submitted
13 Jul 2017
Accepted
24 Aug 2017
First published
24 Aug 2017

Chem. Commun., 2017,53, 10216-10219
Article type
Communication

Asymmetric conjugate addition of alkylzirconium reagents to α,β-unsaturated thioesters: access to fragrances and acyclic stereochemical arrays

Z. Gao and S. P. Fletcher, Chem. Commun., 2017, 53, 10216
DOI: 10.1039/C7CC05433E

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