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Asymmetric Synthesis of Chiral Cyclopentanes Bearing an All‐Carbon Quaternary Stereocenter by Zirconium‐Catalyzed Double Carboalumination
Author(s) -
Xu Shiqing,
Wang Chuan,
Komiyama Masato,
Tomonari Yasuhiko,
Negishi Eiichi
Publication year - 2017
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.201706198
Subject(s) - stereocenter , cyclopentanes , intramolecular force , chemistry , zirconium , enantioselective synthesis , catalysis , tandem , stereochemistry , combinatorial chemistry , organic chemistry , materials science , composite material
Herein, we report a zirconium‐catalyzed enantio‐ and diastereoselective inter/intramolecular double carboalumination of unactivated 2‐substituted 1,5‐dienes, which provides efficient and direct access to chiral cyclopentanes through the generation of two stereocenters, including one all‐carbon quaternary stereocenter, generally with excellent diastereo‐ and high enantioselectivity. This tandem carboalumination process creates two new C−C bonds as well as one C−Al bond, which can be oxidized in situ with O 2 or hydrolyzed. Furthermore, the obtained chiral cyclopentanes can be readily functionalized to provide various chiral compounds.