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Asymmetric One‐Pot Four‐Component Coupling Reaction: Synthesis of Substituted Tetrahydropyrans Catalyzed by Diphenylprolinol Silyl Ether
Author(s) -
Ishikawa Hayato,
Sawano Satoshi,
Yasui Yusuke,
Shibata Yusuke,
Hayashi Yujiro
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.201005386
Subject(s) - tetrahydropyran , chemistry , enantioselective synthesis , silylation , computer science , ring (chemistry) , catalysis , stereochemistry , combinatorial chemistry , organic chemistry
Domino effect : The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.