Synthesis 2013; 45(12): 1641-1646
DOI: 10.1055/s-0033-1338705
special topic
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Direct Vinylogous Michael Addition of γ-Aryl-Substituted Deconjugated Butenolides to Nitroolefins and N-Phenylmaleimide

Vikas Kumar
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India   Fax: +91(80)23600529   Email: sm@orgchem.iisc.ernet.in
,
Bidisha Ray
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India   Fax: +91(80)23600529   Email: sm@orgchem.iisc.ernet.in
,
Preeti Rathi
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India   Fax: +91(80)23600529   Email: sm@orgchem.iisc.ernet.in
,
Santanu Mukherjee*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India   Fax: +91(80)23600529   Email: sm@orgchem.iisc.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 08 March 2013

Accepted after revision: 15 April 2013

Publication Date:
08 May 2013 (eFirst)

Abstract

Direct asymmetric vinylogous Michael reactions of γ-aryl-substituted deconjugated butenolides with nitroolefins and N-phenylmaleimide are described using bifunctional thiourea derivatives as the catalyst. The resulting butenolide derivatives containing adjacent quaternary and tertiary stereocenters are obtained in good yields (54–90%) and with excellent enantioselectivities (er up to 99:1) and high diastereoselectivities (dr up to >20:1).

Supporting Information

 
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