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

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 ter...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1039/C7CC05433E

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Keble College
Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Chemical Communications Journal website
Volume:
53
Issue:
73
Pages:
10216-10219
Publication date:
2017-08-24
Acceptance date:
2017-08-24
DOI:
EISSN:
1364-548X
ISSN:
1359-7345
Pubs id:
pubs:724035
URN:
uri:4a71092d-91c4-4606-8c9f-7a96b0f39870
UUID:
uuid:4a71092d-91c4-4606-8c9f-7a96b0f39870
Local pid:
pubs:724035

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