Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts.

Yasuhiro Sawamura,Yoshihiro Ogura,H. Nakatsuji,A. Sakakura,K. Ishihara

Published 2016 in Chemical Communications

ABSTRACT

Chiral phosphite-urea bifunctional catalysts have been developed for the enantioselective bromocyclization of 2-geranylphenols with N-bromophthalimide (NBP) for the first time. The chiral triaryl phosphite moiety activates NBP to generate a bromophosphonium ion. On the other hand, the urea moiety interacts with a hydroxyl group of the substrate through hydrogen bonding interactions. Enantioselectivity is effectively induced through two-point attractive interactions between the catalyst and the substrate.

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