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Asymmetric Hetero‐Diels–Alder Reaction of Danishefsky’s Diene with α‐Ketoesters and Isatins Catalyzed by a Chiral N , N′ ‐Dioxide/Magnesium(II) Complex
Author(s) -
Zheng Jianfeng,
Lin Lili,
Fu Kai,
Zhang Yulong,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404144
Subject(s) - diene , catalysis , enantioselective synthesis , yield (engineering) , diels–alder reaction , magnesium , chemistry , dihydropyran , organic chemistry , medicinal chemistry , materials science , metallurgy , natural rubber
A highly enantioselective hetero‐Diels–Alder reaction of Danishefsky’s diene with α‐ketoesters and isatins has been realized by using a chiral N , N ′‐dioxide/Mg II complex. In the presence of only 0.1–0.5 mol % catalyst, a series of substrates were transformed into the corresponding tetrasubstituted 2,3‐dihydropyran‐4‐ones in up to 99 % yield and more than 99 % ee in two hours.