Highly Stereoselective Conjugate Additions of Heteroaryl Alkyl Sulfoxides

Mike Casey; Raymond S. Gairns; Gráinne M. Geraghty; Cornelius J. Kelly; Patrick J. Murphy; Andrew J. Walker

doi:10.1055/s-2000-8691

Synlett 2000; 2000(12): 1721-1724
DOI: 10.1055/s-2000-8691

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Highly Stereoselective Conjugate Additions of Heteroaryl Alkyl Sulfoxides

Mike Casey^* , Raymond S. Gairns, Gráinne M. Geraghty, Cornelius J. Kelly, Patrick J. Murphy, Andrew J. Walker

^*Chemistry Department, University College Dublin, Belfield, Dublin 4, Ireland; Fax +353(1)706 24 20; E-mail: mike.casey@ucd.ie

Abstract

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Conjugate additions of alkyl-1-methyl-2-imidazolyl and 2-pyridyl sulfoxides to α,β-unsaturated esters proceeded in high yield and with excellent diastereoselectivity when LHMDS, rather than LDA, was used as the base. Additions to enones were complicated by competitive 1,2-addition. A benzyl imidazolyl sulfoxide underwent selective conjugate addition to an enone, but did not react with unsaturated esters. In contrast, a benzyl 2,4-dimethoxyphenyl sulfoxide gave high yields and stereoselectivity in additions to unsaturated esters.

amide bases - diastereoselectivity - nucleophilic additions - heteroaryl sulfoxides - unsaturated esters

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