Issue 8, 2012
From the journal:

Organic & Biomolecular Chemistry

Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes†

Ramalingam Boobalan,a   Chinpiao Chen*a  and  Gene-Hsian Leeb  

* Corresponding authors

a Department of Chemistry, National Dong Hwa University, Soufeng, Hualien 974, Taiwan, Republic of China
E-mail: chinpiao@mail.ndhu.edu.tw
Fax: 886 3 863 0475
Tel: 886 3 863 3597

b Instrumentation Center, College of Science, National Taiwan University, Taipei 106, Taiwan, Republic of China

Abstract

A series of Schiff base ligands were synthesized from (1R)-camphor. Under the optimal conditions, (+)-SBAIB-a, 10 was found to be an excellent catalyst for the enantioselective addition of phenylacetylene to various aldehydes without utilizing either achiral additives or Ti(OiPr)4. This approach yielded (R)-propargylic alcohols in extremely high yields (up to 99%) and excellent enantioselectivities (up to 92%). The corresponding (S)-propargylic alcohols were synthesized in good to high enantioselectivities (up to 91%) and excellent yields (up to 99%) using (−)-SBAIB-a, 41.

Graphical abstract: Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1OB06683H
Article type
Paper
Submitted
04 Oct 2011
Accepted
11 Nov 2011
First published
16 Nov 2011

Org. Biomol. Chem., 2012,10, 1625-1638

Permissions

Request permissions

Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes

R. Boobalan, C. Chen and G. Lee, Org. Biomol. Chem., 2012, 10, 1625 DOI: 10.1039/C1OB06683H

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements