Synthesis 2013; 45(19): 2662-2668
DOI: 10.1055/s-0033-1339485
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

A Convenient Catalytic Asymmetric Conjugate Addition Reaction to Enones Using Alkylzirconium Reagents

Rebecca M. Maksymowicz
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   Fax: +44(1865)285002   Email: stephen.fletcher@chem.ox.ac.uk
,
Mireia Sidera
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   Fax: +44(1865)285002   Email: stephen.fletcher@chem.ox.ac.uk
,
Philippe M. C. Roth
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   Fax: +44(1865)285002   Email: 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   Fax: +44(1865)285002   Email: stephen.fletcher@chem.ox.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 24 June 2013

Accepted after revision: 03 July 2013

Publication Date:
24 July 2013 (online)

Abstract

Alkylzirconium reagents undergo highly enantioselective copper-catalysed 1,4-addition reaction to cyclic enones. These reactions use alkylmetal species generated in situ from alkenes and the Schwartz reagent, and do not require premade organometallic reagents. The reactions have been performed on practical synthetic scales (2.5 mmol) and a scale-up to 10 mmol is demonstrated. The reactions proceed at room temperature, in a variety of solvents, and tolerate many functional groups.

Supporting Information

 
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