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Rapid entry to enantiopure polycyclic β-lactams via intramolecular nitrone-alkene cycloaddition of 2-azetidinone-tethered alkenylaldehydes

✍ Scribed by Benito Alcaide; Jose M. Alonso; Moustafa F. Aly; Elena Sáez; M. Paz Martínez-Alcázar; Félix Hernández-Cano

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 286 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01013-8

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✦ Synopsis

New enantiomerically pure fused 2 or bridged 3 polycyclic 15-1actam systems are regio-and stereoselectively prepared via intramolecular nitrone-alkene cycloaddition of 2azetidinone-tethered alkenyl-aldehydes 1. The regioselectivity of the cycloaddition can be tuned by moving the alkene substituent from N1 to C3 on the 2-azetidinone ring.

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