Intramolecular conjugate displacement: A general route to hexahydroquinolizines, hexahydroindolizines, and related [m, n, 0]-bicyclic structures with nitrogen at a …

DLJ Clive, Z Li, M Yu

Index: Clive, Derrick L. J.; Li, Zhiyong; Yu, Maolin Journal of Organic Chemistry, 2007 , vol. 72, # 15 p. 5608 - 5617

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Citation Number: 41

Abstract

N-Protected amino aldehydes can be converted into allylic alcohols by the classical Morita- Baylis-Hillman reaction (cf. 2→ 3) or by condensation with selenium-stabilized carbanions, followed by oxidation (cf. 2→ 8→ 3). The derived acetates undergo cyclization when the nitrogen protecting group is removed, affording [m, n, 0]-bicyclic structures with nitrogen at a bridgehead (cf. 4→ 5→ 6). Formation of bicyclic structures via the reactions of Schemes 1 ...