Synthesis 2019; 51(06): 1391-1398
DOI: 10.1055/s-0037-1610337
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of 2,2-Disubstituted Benzofuranones through an Organocatalytic Alkylation with Nitroallylic Acetates

Long Zhao
,
Gerhard Raabe
,
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 09 November 2018

Accepted: 09 November 2018

Publication Date:
30 November 2018 (eFirst)

Abstract

The asymmetric allylic alkylation of benzofuran-3(2H)-ones with nitroallylic acetates has been achieved employing a bifunctional thiourea organocatalyst via SN2′ substitution. A series of 2,2-disubstituted benzofuranones bearing adjacent tetrasubstituted and tertiary stereocenters have been synthesized with moderate to good yields and very good stereoselectivities.

Supporting Information

 
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