Synlett
DOI: 10.1055/s-0036-1589070
letter
© Georg Thieme Verlag Stuttgart · New York

Thiourea-Catalyzed Domino Michael–Mannich [3+2] Cycloadditions: A Strategy for the Asymmetric Synthesis of 3,3′-Pyrrolidinyl-dispirooxindoles

Ying Zhia, Kun Zhaoa, Carolina von Essenb, Kari Rissanenb, Dieter Enders*a
  • aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
  • bDepartment of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
Financial support from the European Research Council (ERC Advanced Grant 320493 ‘DOMINOCAT’) is gratefully acknowledged.
Further Information

Publication History

Received: 22 May 2017

Accepted after revision: 08 June 2017

Publication Date:
13 July 2017 (eFirst)

Dedicated to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

The asymmetric synthesis of trifluoromethylated 3,3′-pyrrolidinyl-dispirooxindole derivatives with four contiguous stereogenic centers, including two vicinal spiro-stereocenters, is described. Employing a bifunctional thiourea catalyst, a domino Michael–Mannich [3+2] cycloaddition occurs readily between isatin ketimines and isatin-derived enoates with good yields and very high stereoselectivities, providing a direct entry to the title compounds of potential medical value.

Supporting Information