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Synthesis of Pyrrolizidine Derivatives by 1,3-Dipolar Cycloaddition Reactions of Chiral Five-Membered Cyclic Azomethine Ylides

✍ Scribed by Nikolaos G. Argyropoulos; Vasiliki C. Sarli; Maria Gdaniec

Book ID: 102177570
Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 163 KB
Volume: 2006
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200600207

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✦ Synopsis

Abstract

The 1,3‐dipolar cycloaddition reactions of chiral five‐membered cyclic azomethine ylides, generated in situ from ethyl glyoxylate and protected (3__S__,4__S__)‐dihydroxypyrrolidines 3 and 6 have been studied. The facial selectivity of the cycloaddition reaction is governed by the steric effect of the substituent on the pyrrolidine ring next to the azomethine ylide functionality, leading in all cases to an exclusive Si face approach of the dipolarophile. The exo/endo selectivity depends on the dipolarophile and on the size of the other substituent on the pyrrolidine ring. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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