How to Make Five Contiguous Stereocenters in One Reaction: Asymmetric Organocatalytic Synthesis of Pentasubstituted Cyclohexanes | Zendy

Reyes Efraím | Zendy; Jiang Hao | Zendy; Milelli Andrea | Zendy; Elsner Petteri | Zendy; Hazell Rita G. | Zendy; Jørgensen Karl Anker | Zendy

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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 %.

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