Synthesis 2016; 48(16): 2595-2602
DOI: 10.1055/s-0035-1561426
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Reformatsky-Type Reaction of Isatin-Derived N-Sulfinyl Ketimines: Efficient and Practical Synthesis of Enantiopure Chiral 2-Oxoindolinyl-β3,3-Amino Esters

Lin Su
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China   Email: xumh@simm.ac.cn
,
Ming-Hua Xu*
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China   Email: xumh@simm.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 16 January 2016

Accepted after revision: 07 March 2016

Publication Date:
18 April 2016 (eFirst)

Abstract

Optically pure 2-oxoindolinyl-β3,3-amino esters were obtained in good yields via highly efficient diastereoselective asymmetric Reformatsky-type reaction of isatin-derived chiral N-sulfinyl ketimines. The method is practical and allows rapid access to various important synthetic intermediates such as N-free 2-oxoindolinyl-β3,3-amino acid, spiro-β-lactam, and hexahydrofurano[2,3-b]indole. It can also be used for the synthesis of gastrin/cholecyctokinin-B receptor antagonist AG-041R.

Supporting Information

 
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