Issue 3, 2006
From the journal:

Chemical Society Reviews

Design and application of linked-BINOL chiral ligands in bifunctional asymmetric catalysis

Masakatsu Shibasaki*a  and  Shigeki Matsunaga*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
E-mail: mshibasa@mol.f.u-tokyo.ac.jp, smatsuna@mol.f.u-tokyo.ac.jp
Fax: (+81)3-5684-5206

Abstract

The design and application of linked-BINOLs investigated in our group are reviewed. Linked-BINOLs are a kind of semi-crown ether, thus they are flexible and applicable to metals having various ionic radii (Ga3+, Li+, Zn2+, In3+, La3+, and Y3+). The flexible linker segment, containing a coordinative heteroatom, has a crucial role in the construction of a unique and effective chiral environment that is not accessible from BINOL itself. Applications of linked-BINOLs to an epoxide opening reaction, Michael reactions, a direct aldol reaction, direct Michael reactions of a hydroxyketone, and direct Mannich-type reactions of hydroxyketones and N-acylpyrrole are described.

Graphical abstract: Design and application of linked-BINOL chiral ligands in bifunctional asymmetric catalysis

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Article information

DOI
https://doi.org/10.1039/B506346A
Article type
Tutorial Review
Submitted
23 Nov 2005
First published
09 Feb 2006

Chem. Soc. Rev., 2006,35, 269-279

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Design and application of linked-BINOL chiral ligands in bifunctional asymmetric catalysis

M. Shibasaki and S. Matsunaga, Chem. Soc. Rev., 2006, 35, 269 DOI: 10.1039/B506346A

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