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Synthesis 2011(21): 3563-3568  
DOI: 10.1055/s-0030-1260226
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Application of Azomethine Ylides in the Synthesis of Carbohydrate-Derived Spiroheterocycles

Piyali Deb Barman, Ishita Sanyal, Sukhendu B. Mandal, Asish Kumar Banerjee*
Department of Chemistry, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India
Fax: +91(33)24735197; e-Mail: ashisbanerjee@iicb.res.in;
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Publication History

Received 28 June 2011
Publication Date:
13 September 2011 (online)

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Abstract

A series of sugar-fused spiro-pyrrolidine, -pyrrolizidine, and -indolizidine heterocycles were synthesized through a unique application of a 1,3-dipolar cycloaddition reaction of an azomethine ylide with a carbohydrate-derived olefin. The 1,3-dipoles synthesized from secondary α-amino acids (sarcosine, proline, or pipecolinic acid) and 1,2-diketones (isatin or acenaphthoquinone), upon reaction with the olefin, gave the corresponding cycloaddition products in good-to-very good yields.

Key words

heterocycles - spiro compounds - carbohydrates - ylides - cycloadditions

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