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

Rebecca M. Maksymowicz; Mireia Sidera; Philippe M. C. Roth; Stephen P. Fletcher

doi:10.1055/s-0033-1339485

Synthesis, Table of Contents

Synthesis 2013; 45(19): 2662-2668
DOI: 10.1055/s-0033-1339485

practical synthetic procedures

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

Abstract

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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.

Key words

alkenes - asymmetric catalysis - copper - Michael addition - Schwartz reagent

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References

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