期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 31, 页码 10733-10741出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04759
关键词
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资金
- Natural Science Foundation of China [21572130]
- China Postdoctoral Science Foundation [2016M590354]
- National Key Basic Research Program of China [2013CB934102]
- Shanghai Jiao Tong University
An efficient method for the enantioselective construction of tertiary C-O bond via asymmetric allylic substitution of racemic vinylethylene carbonates with water and alcohols has been developed. Under the cooperative catalysis system of an in situ generated chiral palladium complex and boron reagent in mild conditions, the process allowed rapid access to valuable tertiary alcohols and ethers in high yields with complete regioselectivities and high. enantioselectivities. This protocol represented the first example of direct enantioselective formation of a tertiary C-O bond with water as an oxygen donor. The synthetic utilities of the process have been demonstrated by the elaboration of the products into key intermediates of biologically relevant agents, and chiral tertiary cyclic ethers could also be provided through the sequential reactions of the allylic etherification and ring-closing metathesis.
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