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Gold-catalyzed oxa-povarov reactions for the synthesis of highly substituted dihydrobenzopyrans from diaryloxymethylarenes and olefins
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Gold-catalyzed oxa-povarov reactions for the synthesis of highly substituted dihydrobenzopyrans from diaryloxymethylarenes and olefins

Vinayak Vishnu Pagar, Chang-Chin Tseng and Rai-Shung Liu
Chemistry - A European Journal, Vol.20(33), pp.10519-10526
11/08/2014

Abstract

cycloaddition diastereoselectivity gold oxygen heterocycles synthetic methods
Oxa-Povarov reactions involving readily available diaryloxymethylarenes and aryl-substituted alkenes are reported. Their [4+2] cycloadditions were efficiently catalyzed by IPrAuSbF 6 (IPr=1,3-bis(diisopropylphenyl) imidazol-2-ylidene) with high diastereoselectivity. Product analysis revealed that the reactions likely proceed by a stepwise ionic mechanism, because both E- and Z-configured β-methylstyrene gave the same cycloadducts in the same proportions. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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