A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes

A cooperative Cu/Pd-catalyzed asymmetric three-component reaction of styrenes, B2(pin)2, and allyl carbonates was reported. This reaction, in the presence of chiral CuOAc/SOP and achiral Pd­(dppf)­Cl2 catalysts, occurs smoothly with high enantioselectivities (up to 97% ee) . The allylboration produc...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-11, Vol.137 (43), p.13760-13763
Main Authors: Jia, Tao, Cao, Peng, Wang, Bing, Lou, Yazhou, Yin, Xuemei, Wang, Min, Liao, Jian
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Boranes - chemical synthesis
Boranes - chemistry
Catalysis
Copper - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
Piperidines - chemical synthesis
Piperidines - chemistry
Stereoisomerism
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Summary:A cooperative Cu/Pd-catalyzed asymmetric three-component reaction of styrenes, B2(pin)2, and allyl carbonates was reported. This reaction, in the presence of chiral CuOAc/SOP and achiral Pd­(dppf)­Cl2 catalysts, occurs smoothly with high enantioselectivities (up to 97% ee) . The allylboration products, which contain alkene (or diene) unite and alkylboron group, are easily functionalized. The utility of this protocol was demonstrated through the synthesis of an antipsychotic drug, (−)-preclamol.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b09146