Issue 2, 2016

Triazole–gold promoted intermolecular propargyl alcohol addition to alkyne: the reaction cascade toward substituted allenes

Abstract

Gold-catalyzed intermolecular propargyl alcohol addition to alkyne was achieved. The reaction of propargyl alcohol with a typical gold catalyst gave the hydration product almost exclusively. The triazole gold catalyst (TA–Au) successfully prevented the hydration, giving the vinyl ether followed by a 3,3-rearrangement. Synthetically useful substituted allenes were formed with high efficiency, substrate tolerability and chemoselectivity. Also, more than 95% chirality transfer from propargyl alcohol to allene was obtained.

Graphical abstract: Triazole–gold promoted intermolecular propargyl alcohol addition to alkyne: the reaction cascade toward substituted allenes

Supplementary files

Article information

Article type
Communication
Submitted
02 Oct 2015
Accepted
20 Oct 2015
First published
21 Oct 2015

Chem. Commun., 2016,52, 296-299

Author version available

Triazole–gold promoted intermolecular propargyl alcohol addition to alkyne: the reaction cascade toward substituted allenes

S. Hosseyni, S. Ding, Y. Su, N. G. Akhmedov and X. Shi, Chem. Commun., 2016, 52, 296 DOI: 10.1039/C5CC08233A

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