Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 51, Pages 20738-20741Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja210025q
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- JSPS [23655082]
- Grants-in-Aid for Scientific Research [23655082] Funding Source: KAKEN
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The stereochemical course of the stereospecific Suzuki-Miyaura coupling of enantioenriched alpha-(acetylamino)benzylboronic esters with aryl bromides can be switched by the choice of acidic additives in the presence of a Pd/XPhos catalyst system. Highly enantiospecific, invertive C-C bond formation takes place with the use of phenol as an additive. In contrast, high enantiospecificity for retention of configuration is attained in the presence of Zr(Oi-Pr)(4)center dot i-PrOH as an additive.
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