Synthesis 2018; 50(22): 4435-4443
DOI: 10.1055/s-0036-1591590
paper
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

Hari P. R. Mangunuru
,
Christian A. Malapit
,
Nizar Haddad*
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
,
Jonathan T. Reeves
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
,
Bo Qu
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
,
Sonia Rodriguez
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
,
Heewon Lee
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
,
Nathan K. Yee
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
,
Jinhua J. Song
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
,
Carl A. Busacca
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
,
Chris H. Senanayake*
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA   Email: nizar.haddad@boehringer-ingelheim.com
› Author Affiliations
Further Information

Publication History

Received: 13 March 2018

Accepted after revision: 27 April 2018

Publication Date:
28 June 2018 (eFirst)

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday

Abstract

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i-Pr-BI-DIME and Me2-BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd2(dba)3/i-Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me2-BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

Supporting Information

 
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