Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides | Zendy

Bowman Potter | Zendy; Adam A. Szymaniak | Zendy; Emma K. Edelstein | Zendy; James P. Morken | Zendy

Open Access

Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides

Author(s) -

Bowman Potter,

Adam A. Szymaniak,

Emma K. Edelstein,

James P. Morken

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja510266x

Subject(s) - chemistry , allylic rearrangement , geminal , nitrosobenzene , transmetalation , hydrogen peroxide , catalysis , organic chemistry

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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