Harmony of CdI2 with CuBr for the one-pot synthesis of optically active α-allenols

Jiasheng Zhang; Juntao Ye; Shengming Ma

doi:10.1039/C4OB02673J

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

Harmony of CdI₂ with CuBr for the one-pot synthesis of optically active α-allenols†

Jiasheng Zhang,^a Juntao Ye^a and Shengming Ma*^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China
E-mail: masm@sioc.ac.cn
Fax: (+86)-21-64167510

^b Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200322, P. R. China

Abstract

A highly efficient one-pot synthesis of chiral α-allenols from propargylic alcohols, aldehydes and pyrrolidine induced by CuBr and (R,R_a)-N-PINAP or (R,S_a)-N-PINAP and CdI₂ has been developed. Both the yields and enantioselectivities of the allenols of this one-pot procedure are practical. Comparison with ZnI₂ control experiments revealed that CdI₂ can convert propargylic amine to allene in the presence of CuBr efficiently.

Download options Please wait...

Supplementary files

Supplementary information PDF (23316K)

Article information

DOI: https://doi.org/10.1039/C4OB02673J
Article type: Paper
Submitted: 27 Dec 2014
Accepted: 02 Feb 2015
First published: 03 Feb 2015
This article is Open Access

Download Citation

Org. Biomol. Chem., 2015,13, 4080-4089

Permissions

Request permissions

Harmony of CdI₂ with CuBr for the one-pot synthesis of optically active α-allenols

J. Zhang, J. Ye and S. Ma, Org. Biomol. Chem., 2015, 13, 4080 DOI: 10.1039/C4OB02673J

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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.

Organic & Biomolecular Chemistry