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How to Make Five Contiguous Stereocenters in One Reaction: Asymmetric Organocatalytic Synthesis of Pentasubstituted Cyclohexanes
Author(s) -
Reyes Efraím,
Jiang Hao,
Milelli Andrea,
Elsner Petteri,
Hazell Rita G.,
Jørgensen Karl Anker
Publication year - 2007
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.200704454
Subject(s) - stereocenter , dabco , diastereomer , cyclohexanes , chemistry , domino , organocatalysis , octane , stereochemistry , cascade reaction , organic chemistry , enantioselective synthesis , catalysis
Give me five! An organocatalyzed two‐component domino reaction has been developed in which two new CC bonds and five stereocenters are created in a one‐pot fashion (see scheme; DABCO=1,4‐diazabicyclo[2.2.2]octane, TMS=trimethylsilyl). The striking features of this transformation are the high preference for one diastereomer (out of 32 possible isomers) and enantioselectivities of up to 94 %.