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Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, P.R. China
E-mail: mxzhao@ecust.edu.cn
; Fax: +86-21-34201699
b
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P.R. China
E-mail: Mshi@mail.sioc.ac.cn
; Fax: +86-21-64166128
Org. Biomol. Chem., 2012,10, 7970-7979
DOI:
10.1039/C2OB25966D
Received
19 May 2012,
Accepted
02 Aug 2012
First published online
02 Aug 2012
A highly enantioselective Michael addition of 3-aryloxindole to vinyl bisphosphonate ester catalyzed by a cinchonidine derived thiourea catalyst has been investigated. The corresponding adducts, containing a chiral quaternary carbon center and geminal bisphosphonate ester fragment at the 3-position of the oxindole, were obtained in moderate to good yields (65–92%) and moderate to good enantioselectivities (up to 92% ee).