期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 4, 页码 1704-1709出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b11529
关键词
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资金
- United States National Institutes of Health, Institute of General Medical Sciences [R01GM116987]
- University of North Carolina at Chapel Hill
- National Science Foundation [CHE1726291]
A Cu-catalyzed method for the efficient enantio- and diastereoselective synthesis of chiral homoallylic amines bearing a quaternary carbon and an alkenylboron is disclosed. Transformations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable gamma,gamma-disubstituted allyldiborons and benzyl imines; products are obtained in up to 82% yield, >20:1 dr, and >99:1 er. Reactions proceed via stereodefined boron-stabilized allylic Cu species formed by an enantioselective transmetalation. Utility of the 1-amino-3-alkenylboronate products is highlighted by a variety of synthetic transformations.
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