Novel Regio- and Stereoselective
Synthesis of Functionalized 3-Spiropyrrolidines and 3-Spiropyrrolizidines
Using the Baylis-Hillman Adducts Derived from
Nitroolefins

Manickam Bakthadoss; Nagappan Sivakumar

doi:10.1055/s-0028-1088206

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Synlett 2009(6): 1014-1018
DOI: 10.1055/s-0028-1088206

LETTER

Novel Regio- and Stereoselective Synthesis of Functionalized 3-Spiropyrrolidines and 3-Spiropyrrolizidines Using the Baylis-Hillman Adducts Derived from Nitroolefins

Manickam Bakthadoss*, Nagappan Sivakumar
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, Tamilnadu, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;

Further Information

Publication History

Received 2 October 2008
Publication Date:
16 March 2009 (online)

Abstract
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Abstract

A facile regio- and stereoselective synthesis of functionalized 3-spiropyrrolidines and 3-spiropyrrolizidines using the Baylis-Hillman adducts derived from nitroolefins via intermolecular [3+2] cycloaddition reaction is reported.

Key words

Baylis-Hillman reaction - intermolecular [3+2] cycloaddition - azomethine ylides - 1,3-dipolar cycloaddition - spiro compounds

References and Notes

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The X-ray crystal structure data of 6a and 7d have been deposited at the Cambrigde Crystallographic Data Centre and allocated the deposition numbers CCDC 676397 (6a), and CCDC 676668 (7d). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.