期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 52, 页码 17918-17921出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja510266x
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资金
- NIH [GM-59471]
Under the influence of a chiral palladium catalyst, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate nonracemic allyl boronates with high levels of enantioselectivity. The so-formed allyl boronates may be oxidized with hydrogen peroxide to provide secondary allylic alcohols or with nitrosobenzene to furnish nonracemic tertiary allylic alcohols. Mechanistic experiments suggest the operation of a pathway involving outer-sphere stereoinvertive transmetalation.
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