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Enantioselective Synthesis of cis ‐Decalin Derivatives by the Inverse‐Electron‐Demand Diels–Alder Reaction of 2‐Pyrones
Author(s) -
Si XuGe,
Zhang ZhiMao,
Zheng ChengGong,
Li ZhanTing,
Cai Quan
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202006841
Subject(s) - enantioselective synthesis , stereocenter , decalin , silylation , chemistry , diastereomer , oxonium ion , total synthesis , stereochemistry , catalysis , organic chemistry , ion
A novel strategy for the synthesis of cis ‐decalins by an ytterbium‐catalyzed asymmetric inverse‐electron‐demand Diels–Alder reaction of 2‐pyrones and silyl cyclohexadienol ethers is reported here. A broad range of synthetically important cis ‐decalin derivatives with multiple contiguous stereogenic centers and functionalities are obtained in good yields and stereoselectivities. A full set of diastereomeric substituted cis ‐decalin motifs are readily accessible by tuning the absolute configurations of substituted silyl cyclohexadienol ethers ( R or S ) as well as the ligands ( R or S ). The synthetic potential is showcased by the enantioselective total synthesis of 4‐amorphen‐11‐ol, and further demonstrated by the first total synthesis of cis ‐crotonin.