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September 7, 2010Journal of the American Chemical Society267 citations

Stereospecific Suzuki−Miyaura Coupling of Chiral α-(Acylamino)benzylboronic Esters with Inversion of Configuration

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TOToshimichi OhmuraTATomotsugu AwanoMSMichinori Suginome

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Abstract

The first invertive B-alkyl Suzuki-Miyaura coupling has been achieved. The coupling of enantioenriched α-(acylamino)benzylboronic esters with aryl bromides and chlorides took place efficiently in toluene at 80 °C in the presence of Pd(dba)(2) (5 mol %), XPhos (10 mol %), K(2)CO(3) (3 equiv), and H(2)O (2 equiv). The reaction proceeded with inversion of configuration to give diarylmethanamine derivatives in high yields with high conservation of enantiomeric excesses.

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Cite This Study

Ohmura et al. (2010) studied this question.

synapsesocial.com/papers/69dd4ed03f27c4971e99b3e2https://doi.org/10.1021/ja106632j
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