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. 2009 Apr 15;131(14):5024-5.
doi: 10.1021/ja8094075.

Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration

Daisuke Imao  1 , Ben W Glasspoole, Véronique S Laberge, Cathleen M Crudden
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Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration

Daisuke Imao et al. J Am Chem Soc. .

Abstract

We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes. In order for the reaction to take place in high yields, the use of silver oxide as a base and the presence of at least 8 equiv of triphenyl phosphine per Pd are required. The reaction proceeds with >90% retention of configuration in all cases except one. Remarkably, the linear boronate ester does not react under these conditions.

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