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Asymmetric conjugate addition of alkylzirconium reagents to α,β-unsaturated lactones.

Abstract:
The asymmetric synthesis of β-substituted lactones by catalytic asymmetric conjugate addition of alkyl groups to α,β-unsaturated lactones is reported. The method uses alkylzirconium nucleophiles prepared in situ from alkenes and the Schwartz reagent. Enantioselective additions to 6- and 7-membered lactones proceed at rt, tolerate a wide variety of functional groups, and are readily scalable. The method was used in a formal asymmetric synthesis of mitsugashiwalactone.
Publication status:
Published

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Publisher copy:
10.1021/ol501292x

Authors


Maciver, EE More by this author
Maksymowicz, RM More by this author
Wilkinson, N More by this author
Fletcher, SP More by this author
Publisher:
American Chemical Society
Journal:
Organic letters
Volume:
16
Issue:
12
Pages:
3288-3291
Publication date:
2014-06-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:82c97eea-55f1-48bc-bf48-906e8a364fea
Source identifiers:
469553
Local pid:
pubs:469553
Language:
English

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