Side-Arm-Promoted Highly Enantioselective Ring-Opening Reactions and Kinetic Resolution of Donor–Acceptor Cyclopropanes with Amines

A Ni-catalyzed asymmetric ring-opening reaction of 2-substituted cyclopropane-1,1-dicarboxylates with aliphatic amines has been accomplished using the chiral indane–trisoxazoline (In-TOX) ligand. This highly enantioselective reaction provides an efficient approach to a variety of chiral γ-substitute...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-06, Vol.134 (22), p.9066-9069
Main Authors: Zhou, You-Yun, Wang, Li-Jia, Li, Jun, Sun, Xiu-Li, Tang, Yong
Format: Article
Language:English
Subjects:
Amines - chemistry
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Crystallography, X-Ray
Cyclopropanes - chemistry
Kinetics
Models, Molecular
Molecular Structure
Nickel - chemistry
Organometallic Compounds - chemistry
Stereoisomerism
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Summary:A Ni-catalyzed asymmetric ring-opening reaction of 2-substituted cyclopropane-1,1-dicarboxylates with aliphatic amines has been accomplished using the chiral indane–trisoxazoline (In-TOX) ligand. This highly enantioselective reaction provides an efficient approach to a variety of chiral γ-substituted γ-amino acid derivatives, which are readily transformed into multifunctionalized piperidines and γ-lactams. The single-crystal X-ray structure of the TOX–Ni complex is provided, and the role of the side arm in the chiral ligand is discussed.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja302691r