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Copper‐Catalyzed Enantioselective Inverse Electron‐Demand Hetero‐Diels–Alder Reactions of Diazadienes with Enol Ethers: Efficient Synthesis of Chiral Pyridazines
Author(s) -
Gao Shuang,
Chen JiaRong,
Hu XiaoQiang,
Cheng HongGang,
Lu LiangQiu,
Xiao WenJing
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300723
Subject(s) - enantioselective synthesis , chemistry , pyridazine , enol , catalysis , diels–alder reaction , organic chemistry , combinatorial chemistry
Abstract A highly efficient and enantioselective inverse electron‐demand hetero‐Diels–Alder reaction of in situ generated 1,2‐diaza‐1,3‐dienes with enol ethers has been developed with the use of a chiral copper/bisoxazoline complex as the catalyst. The reaction exhibits high enantioselectivity (up to 90% ee ) and provides a robust and powerful method to synthesize a variety of structurally diverse and densely substituted chiral pyridazine derivatives in good to excellent yields.