Journal of the American Chemical Society 2013-03-13

Enantioselective synthesis of multisubstituted biaryl skeleton by chiral phosphoric acid catalyzed desymmetrization/kinetic resolution sequence.

Keiji Mori, Yuki Ichikawa, Manato Kobayashi, Yukihiro Shibata, Masahiro Yamanaka, Takahiko Akiyama

Index: J. Am. Chem. Soc. 135(10) , 3964-70, (2013)

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Abstract

Described herein is the enantioselective synthesis of multisubstituted biaryl derivatives by chiral phosphoric acid catalyzed asymmetric bromination. Two asymmetric reactions (desymmetrization and kinetic resolution) proceeded successively to afford chiral biaryls in excellent enantioselectivities (up to 99% ee). Both experimental and computational studies suggested that this excellent selectivity could be achieved via a highly organized hydrogen bond network among a substrate, a catalyst (chiral phosphoric acid), and a brominating reagent (N-bromophthalimide).