Development of a New Dimeric Cyclophane Ligand:  Application to Enhanced Diastereo- and Enantioselectivity in the Catalytic Synthesis of β-Lactams

We detail the synthesis of a new C 2-symmetric bis(cyclophane) ligand system that can be thought of as electronically analogous to binol, but which possesses the added “third dimension” of cyclophane chirality. The ligand synthesis involves a spontaneous (but unexpected) atropisomerization to the de...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-06, Vol.69 (13), p.4531-4533
Main Authors: Wack, Harald, France, Stefan, Hafez, Ahmed M, Drury, William J, Weatherwax, Anthony, Lectka, Thomas
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Dimerization
Ethers, Cyclic - chemical synthesis
Exact sciences and technology
General and physical chemistry
Lactams - chemical synthesis
Ligands
Models, Molecular
Molecular Structure
Naphthols - chemistry
Stereoisomerism
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:We detail the synthesis of a new C 2-symmetric bis(cyclophane) ligand system that can be thought of as electronically analogous to binol, but which possesses the added “third dimension” of cyclophane chirality. The ligand synthesis involves a spontaneous (but unexpected) atropisomerization to the desired product. We have employed this ligand to form a metal complex that is an effective cocatalyst for the highly enantio- and diastereoselective catalytic asymmetric synthesis of a β-lactam.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049804d