1,3-Dipolar Cycloaddition on
Baylis-Hillman Adducts: Novel Synthesis of Pyrrolidines,
Spiropyrrolidines, and Spiropyrrolizidines

Manickam Bakthadoss; Nagappan Sivakumar; Anthonisamy Devaraj; Duddu S. Sharada

doi:10.1055/s-0030-1260053

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Synthesis 2011(13): 2136-2146
DOI: 10.1055/s-0030-1260053

PAPER

1,3-Dipolar Cycloaddition on Baylis-Hillman Adducts: Novel Synthesis of Pyrrolidines, Spiropyrrolidines, and Spiropyrrolizidines

Manickam Bakthadoss*^a, Nagappan Sivakumar^a, Anthonisamy Devaraj^a, Duddu S. Sharada^b
^a Dept. of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;
^b Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, Tamil Nadu, India

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Publication History

Received 12 February 2011
Publication Date:
19 May 2011 (online)

Abstract
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Abstract

A facile regio- and stereoselective synthesis of functionalized pyrrolidines, spiropyrrolidines, and 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 - pyrrolidines - spiro compounds

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19

The X-ray crystal structure data of 8d, 9a, 10d, and 11a have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 812105 (8d), 676397 (9a), 676668 (10d), and 812104 (11a).