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One-Pot Preparation of Chiral Carbacycles from Morita-Baylis-Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence

Publikace na Přírodovědecká fakulta |
2014

Tento text není v aktuálním jazyce dostupný. Zobrazuje se verze "en".Abstrakt

An operationally simple, one-pot synthetic protocol for the formation of all-carbon, highly substituted five- and six-membered rings is described. In this two-step procedure, an asymmetric allylic alkylation (AAA) of Morita-Baylis-Hillman (MBH) carbonates with allylmalononitrile, catalyzed by a chiral tertiary amine, is followed by a ring-closing alkene metathesis (RCM) reaction.

Products are obtained in high yields, and an excellent level of optical purity of some of the target compounds is achieved after just a single recrystallization.