期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 144, 期 14, 页码 6173-6179出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c01656
关键词
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资金
- NIH [GM-128695]
- Sloan Foundation
- Boston College
Here, we present a catalytic method for the selective coupling of alkyl ethers and heterodienes, enabling the rapid synthesis of dihydropyran derivatives with multiple stereocenters.
We disclose a catalytic method for the enantio- and diastereoselective union of alkyl ethers and heterodienes. Wedemonstrate that a chiral Cu-BOX complex catalyzes the efficient oxidation of ethers into enol ethers in the presence of tritylacetate. Then, the organocopper promotes stereoselective hetero Diels-Alder reaction between thein situgenerated enol ethers and beta,gamma-unsaturated ketoesters, allowing for rapid access to an array of dihydropyran derivatives possessing three vicinal stereogeniccenters.
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