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A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives

✍ Scribed by Steven M Allin; Christopher J Northfield; Michael I Page; Alexandra M.Z Slawin

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 195 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00686-2

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✦ Synopsis

Condensation of 2-formylbenzoic acid with a-amino alcohol substrates proceeds with extremely high diaslereoselectivity to produce tricyclic T-lactam pn~lucts. The relative slereochemislxy of the major diasmreoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical oulcome. Further, we report that this class of heterocycle can act as an Nacyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives.

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