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Synthesis 2012(5): 793-799  
DOI: 10.1055/s-0031-1289704
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Novel Vicinal Coumarin- and Oxindole-Functionalized Dispiropyrrolidines and Dispiropyrrolizidines via [3+2]-Cycloaddition Reactions

Manickam Bakthadoss*, Damodharan Kannan, Govindan Sivakumar
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Fax: +91(44)22352492; e-Mail: bhakthadoss@yahoo.com;
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Publication History

Received 2 November 2011
Publication Date:
15 February 2012 (online)

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Abstract

The synthesis of novel vicinal coumarin- and oxindole-functionalized dispiropyrrolidines and dispiropyrrolizidines containing three and four contiguous stereogenic centers, respectively, has been accomplished in excellent yields and with high regio- and stereoselectivity. The dispiro compounds are obtained via [3+2]-cycloaddition reactions between (E)-3-benzylidenechroman-2-one and the adduct generated from isatin and N-methylglycine or l-proline.

Key words

coumarins - oxindoles - Baylis-Hillman adducts - dispiropyrrolidines - dispiropyrrolizidines - stereoselectivity

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9

Crystal data for compounds 10a and 13a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 764210 and CCDC 833470, respectively, and can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk; or via www.ccdc.cam.uk/conts/retrieving.html