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Enantioselective Amine‐Catalyzed [4+2] Annulations of Allenoates and Oxo‐dienes: An Asymmetric Synthesis of Dihydropyrans
Author(s) -
Wang Xiaojun,
Fang Tong,
Tong Xiaofeng
Publication year - 2011
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.201100945
Subject(s) - enantioselective synthesis , amine gas treating , substrate (aquarium) , chemistry , catalysis , outcome (game theory) , scheme (mathematics) , organic chemistry , combinatorial chemistry , mathematics , biology , ecology , mathematical economics , mathematical analysis
Biologically significant polysubstituted dihydropyrans have been prepared in high to excellent yields and enantioselectivities (see scheme). The interaction between functional groups in the zwitterionic intermediate, which is generated by addition of the amine catalyst to the allenoate substrate, is thought to play a crucial role in the stereochemical outcome. Bn=benzyl, DMAP=4‐dimethylaminopyridine.