Novel use of N-benzoyl-N,O-acetals as N-acylimine equivalents in asymmetric heterocycloaddition: an extended enantioselective pathway to beta-benzamido aldehydes

The Journal of Organic Chemistry
P GizeckiG Dujardin

Abstract

For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl(4)-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

Citations

Sep 24, 2009·Chemical Communications : Chem Comm·David S LaitarGeoffrey W Coates
May 5, 2012·Organic & Biomolecular Chemistry·Carlos J SaavedraRosendo Hernández
Jun 25, 2014·Chemistry, an Asian Journal·Boris Egart, Constantin Czekelius
Aug 13, 2021·Accounts of Chemical Research·Kuan Zheng, Ran Hong
Sep 29, 2020·The Journal of Organic Chemistry·Kuan ZhengRan Hong
Dec 7, 2013·Organic Letters·Min LiShijun Wen
Dec 27, 2017·Organic Letters·Philipp KramerGeorg Manolikakes

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