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Highly Enantioselective Rh‐Catalyzed Intramolecular Alder–Ene Reactions for the Syntheses of Chiral Tetrahydrofurans
Author(s) -
Lei Aiwen,
He Minsheng,
Wu Shulin,
Zhang Xumu
Publication year - 2002
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 - 10.1002/1521-3773(20020916)41:18<3457::aid-anie3457>3.0.co;2-3
Subject(s) - intramolecular force , ene reaction , enantioselective synthesis , catalysis , chemistry , diels–alder reaction , medicinal chemistry , organic chemistry
Over 99 % ee was obtained for all the tested substrates in a Rh‐catalyzed Alder–ene reaction. Simply mixing air‐stable, commercially available [{Rh(cod)Cl} 2 ] (cod=1,5‐cyclooctadiene) and 2,2′‐bis(diphenylphosphanyl)‐1,1′‐binaphthyl (binap) at room temperature afforded functionalized and chiral tetrahydrofurans in high yields with high efficiency (turnover frequency: 1500 h −1 ). The catalyst loading was as low as 0.8 mol %.