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Chiral imines on the wave: reactivity of tert-butyl acrylate and stereoselectivity determination using NMR in liquid crystals
Published:
04 December 2015
by MDPI
in MOL2NET'15, Conference on Molecular, Biomedical & Computational Sciences and Engineering, 1st ed.
congress CHEMXEDIT-01, Chem. Exp., Edu., & Info. Tech., Bilbao, Spain-Paris, France, 2015
Abstract:
In connection with synthetic applications, we have foreseen to study the reactivity of the poorly reactive tert-butyl acrylate electrophile with chiral imines of unsymmetrical ketones, using conventional or microwave flash heating under carefully controlled reaction conditions in order to develop a very quick and efficient access to the corresponding Michael adducts in which a created stereogenic quaternary carbon center was fully stereocontrolled. Depending on the conditions, either a keto ester or a lactam were obtained. A good correlation was obtained between experiment and theoretical calculations. . The stereoselectivity of the process (e>95%) was determined using natural abundance 13C-{1H} NMR in a chiral polypeptide liquid crystal.
Keywords: Aza-ene process, Asymmetric Michael reaction, Enamine activation, Unsymmetrical ketones, tert-butyl acrylate, Quaternary carbon center