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Theoretical study of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindole] compounds by [3+2] cycloaddition

Theoretical study of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindole]... Study of the structures of a series of spiro [pyrrolidine-2,3′-oxindole] derivatives synthesized by [3+2] cycloaddition reaction of isatin, α-amino acids, and β-substituted phenylethylenes revealed the regioselectivity of the reaction was completely novel. The reaction mechanism for [3+2] cycloaddition of oxindole azomethine ylide and the β-substituted phenylethylenes was calculated by use of density functional theory with the B3LYP functional and different basis sets. The results show that the regioselectivity of this [3+2] cycloaddition reaction is kinetically controlled, which agrees with experimental results. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Theoretical study of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindole] compounds by [3+2] cycloaddition

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References (10)

Publisher
Springer Journals
Copyright
Copyright © 2014 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
DOI
10.1007/s11164-014-1582-0
Publisher site
See Article on Publisher Site

Abstract

Study of the structures of a series of spiro [pyrrolidine-2,3′-oxindole] derivatives synthesized by [3+2] cycloaddition reaction of isatin, α-amino acids, and β-substituted phenylethylenes revealed the regioselectivity of the reaction was completely novel. The reaction mechanism for [3+2] cycloaddition of oxindole azomethine ylide and the β-substituted phenylethylenes was calculated by use of density functional theory with the B3LYP functional and different basis sets. The results show that the regioselectivity of this [3+2] cycloaddition reaction is kinetically controlled, which agrees with experimental results.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Mar 27, 2014

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