Catalytic asymmetric Diels-Alder reactions involving aryl vinyl ketones

摘要

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.