期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 21, 页码 8982-8987出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja302520h
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资金
- CREST
- JST
- JSPS
- Uehara Memorial Foundation
- MEXT through Global COE [B01]
- Grants-in-Aid for Scientific Research [24685015] Funding Source: KAKEN
The stereochemical courses of the copper-catalyzed allyl-alkyl coupling between enantioenriched chiral allylic phosphates and alkylboranes were switchable between 1,3-anti and 1,3-syn selectivities by the choice of solvents and achiral alkoxide bases with different steric demands. The reactions with gamma-silylated allylic phosphates allow efficient synthesis of enantioenriched chiral allylsilanes with tertiary or quaternary carbon stereogenic centers. Cyclic and acyclic bimodal participation of alkoxyborane species in an organocopper addition-elimination sequence is proposed to account for the phenomenon of the anti/syn-stereochemical reversal.
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