Spiro-2,2′-bichroman-based bisoxazoline (SPANbox) ligands for ZnII-catalyzed enantioselective hydroxylation of β-keto esters and 1,3-diester

Jie Li; Gang Chen; Zheng Wang; Ruzhou Zhang; Xumu Zhang; Kuiling Ding

doi:10.1039/C0SC00607F

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Spiro-2,2′-bichroman-based bisoxazoline (SPANbox) ligands for Zn^II-catalyzed enantioselective hydroxylation of β-keto esters and 1,3-diester†

Jie Li,^a Gang Chen,^a Zheng Wang,^a Ruzhou Zhang,^a Xumu Zhang^ab and Kuiling Ding*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, P. R. China
E-mail: kding@mail.sioc.ac.cn
Fax: + (21)-6416-6128

^b Department of Chemistry and Chemical Biology, Center of Molecular Catalysis, The State University of New Jersey, 610 Taylor, Piscataway, New Jersey, USA

Abstract

A new type of spiro bisoxazoline ligand (SPANbox) has been developed on the basis of the spiro-2,2′-bichroman motif and bisoxazoline chelating units. The Zn(II) complexes of SPANbox showed excellent activity (98–99% yield) and enantioselectivity (90–98% ee) in the catalysis of hydroxylation of various β-keto esters and 1,3-diester with catalyst loading of 0.1–5 mol%. The performance of SPANbox in the present catalytic system was found to be significantly superior to the commonly used classic bisoxazoline ligands, such as (R,R)-Ph-Box or (S,S)-tBu-PyBox, indicating the advantage of the present spiro ligand skeleton.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C0SC00607F
Article type: Edge Article
Submitted: 03 Dec 2010
Accepted: 11 Mar 2011
First published: 30 Mar 2011

Download Citation

Chem. Sci., 2011,2, 1141-1144

Permissions

Request permissions

Spiro-2,2′-bichroman-based bisoxazoline (SPANbox) ligands for Zn^II-catalyzed enantioselective hydroxylation of β-keto esters and 1,3-diester

J. Li, G. Chen, Z. Wang, R. Zhang, X. Zhang and K. Ding, Chem. Sci., 2011, 2, 1141 DOI: 10.1039/C0SC00607F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Science