Congested C–C Bonds by Pd-Catalyzed Enantioselective Allyl–Allyl Cross-Coupling, a Mechanism-Guided Solution

MJ Ardolino, JP Morken

Index: Ardolino, Michael J.; Morken, James P. Journal of the American Chemical Society, 2014 , vol. 136, # 19 p. 7092 - 7100

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Citation Number: 17

Abstract

Under the influence of a chiral bidentate diphosphine ligand, the Pd-catalyzed asymmetric cross-coupling of allylboron reagents and allylic electrophiles establishes 1, 5-dienes with adjacent stereocenters in high regio-and stereoselectivity. A mechanistic study of the coupling utilizing reaction calorimetry and density functional theory analysis suggests that the reaction operates through an inner-sphere 3, 3′-reductive elimination pathway, ...