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.
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Journal Name:Chemical Communications
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CAS no.: 89640-58-4