Nonstabilized N-unsubstituted azomethine ylides: A synthesis of indolizidine 239CD

Authors
Clark, RB Pearson, WH
Citation
Rb. Clark et Wh. Pearson, Nonstabilized N-unsubstituted azomethine ylides: A synthesis of indolizidine 239CD, ORG LETT, 1(2), 1999, pp. 349-351
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
2
Year of publication
1999
Pages
349 - 351
Database
ISI
SICI code
1523-7060(19990729)1:2<349:NNAYAS>2.0.ZU;2-C
Abstract
[GRAPHICS] Treatment of a (2-azaallyl)stannane with HF . pyridine generated a nonstabi lized N-unsubstituted azomethine ylide, which was found to undergo an effic ient and stereoselective dipolar cycloaddition with phenyl vinyl sulfone to produce a trans 2,5-dialkylpyrrolidine that was further transformed into t he dendrobatid alkaloid indolizidine 239CD.