Synthesis 2015; 47(15): 2217-2222
DOI: 10.1055/s-0034-1379928
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Conjugate Addition of Alkylzirconocenes to Cyclopent-4-ene-1,3-dione Monoacetals

Emeline Rideau
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   stephen.fletcher@chem.ox.ac.uk
,
Florian Mäsing
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   stephen.fletcher@chem.ox.ac.uk
,
Stephen P. Fletcher*
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   stephen.fletcher@chem.ox.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 27 March 2015

Accepted after revision: 06 May 2015

Publication Date:
01 July 2015 (eFirst)

Abstract

Copper-catalyzed asymmetric conjugate additions are powerful reactions that allow the formation of single-enantiomer building blocks in a few steps. However, highly enantioselective conjugate addition to five-membered-ring substrates is more challenging and is often neglected. Here, we report catalytic asymmetric 1,4-addition of alkylzirconocenes, formed in situ from readily available alkenes, to cyclopent-4-ene-1,3-dione monoacetals. Good to high enantioselectivities are observed and the procedure tolerates various functional groups.

Supporting Information

 
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