Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): scope, mechanism, and applications

…, HC Shen, L Dong, JP Surivet, C Sylvain

Index: Trost, Barry M.; Shen, Hong C.; Dong, Li; Surivet, Jean-Philippe; Sylvain, Catherine Journal of the American Chemical Society, 2004 , vol. 126, # 38 p. 11966 - 11983

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Citation Number: 135

Abstract

The Pd-catalyzed asymmetric allylic alkylation (AAA) of phenol allyl carbonates serves as an efficient strategy to construct the allylic CO bond allowing access to chiral chromans in up to 98% ee. The effect of pH and the influence of olefin geometry, as well as substitution pattern on the ee and the absolute configuration of the chiral chromans were explored in detail. These observations suggest a mechanism involving the cyclization of the more reactive π- ...