Catalytic asymmetric Diels–Alder reactions involving aryl vinyl ketones?

Chemical Communications Pub Date: 2014-09-19 DOI: 10.1039/C4CC06837H

Abstract

A catalytic asymmetric Diels–Alder reaction of an aryl vinyl ketone with 1,3-dienylcarbamate has been developed. Cyclohexenes bearing vicinal amino and aroyl groups in a cis-configuration were prepared in excellent ee (>99%) and endo (single diastereomer) selectivity. The absolute configuration of one DA product was unambiguously confirmed using XRD analysis. The transition state structure was proposed on the basis of DFT calculations.

Graphical abstract: Catalytic asymmetric Diels–Alder reactions involving aryl vinyl ketones
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