Enantioselective Organocopper-Catalyzed Hetero Diels–Alder Reaction through in Situ Oxidation of Ethers into Enol Ethers | Zendy

Ahmet Yeşilçimen | Zendy; NaChuan Jiang | Zendy; Felix H. Gottlieb | Zendy; Masayuki Wasa | Zendy

Open Access

Enantioselective Organocopper-Catalyzed Hetero Diels–Alder Reaction through in Situ Oxidation of Ethers into Enol Ethers

Author(s) -

Ahmet Yeşilçimen,

NaChuan Jiang,

Felix H. Gottlieb,

Masayuki Wasa

Publication year - 2022

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/jacs.2c01656

Subject(s) - chemistry , enol , stereocenter , enantioselective synthesis , catalysis , dihydropyran , stereoselectivity , organic chemistry , vicinal , diels–alder reaction , enol ether , alkyl

We disclose a catalytic method for the enantio- and diastereoselective union of alkyl ethers and heterodienes. We demonstrate that a chiral Cu-BOX complex catalyzes the efficient oxidation of ethers into enol ethers in the presence of trityl acetate. Then, the organocopper promotes stereoselective hetero Diels-Alder reaction between the in situ generated enol ethers and β,γ-unsaturated ketoesters, allowing for rapid access to an array of dihydropyran derivatives possessing three vicinal stereogenic centers.

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