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

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: [phone]; e-mail: [e-mail]; or via www.ccdc.cam.uk/conts/retrieving.html