Issue 29, 2011
From the journal:

Chemical Communications

Direct substitution of the hydroxy group with highly functionalized nitrogen nucleophiles catalyzed by Au(iii)†

Takashi Ohshima,*a   Yasuhito Nakahara,b   Junji Ipposhi,b   Yoshiki Miyamotob  and  Kazushi Mashima*b  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Kyushu University and CREST, JST, Fukuoka, Japan
E-mail: ohshima@phar.kyushu-u.ac.jp
Fax: +81 92 642 6650
Tel: +81 92 642 6650

b Department of Chemistry, Graduate School of Engineering Science, Osaka University and CREST, JST, Osaka, Japan
E-mail: mashima@chem.es.osaka-u.ac.jp
Fax: +81 6 6850 6245
Tel: +81 6 6850 6245

Abstract

A direct catalytic substitution of various allylic and benzylic alcohols with synthetically useful, but acid-sensitive Boc, Bus, and Dios protected amine nucleophiles, which have not been well utilized for Lewis acid catalysis, with various functionalities (OTBS, OTHP, etc.) was efficiently catalyzed by 1 mol% of Au(III) under mild conditions.

Graphical abstract: Direct substitution of the hydroxy group with highly functionalized nitrogen nucleophiles catalyzed by Au(iii)

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Article information

DOI
https://doi.org/10.1039/C1CC12760H
Article type
Communication
Submitted
11 May 2011
Accepted
31 May 2011
First published
21 Jun 2011

Chem. Commun., 2011,47, 8322-8324

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Direct substitution of the hydroxy group with highly functionalized nitrogen nucleophiles catalyzed by Au(III)

T. Ohshima, Y. Nakahara, J. Ipposhi, Y. Miyamoto and K. Mashima, Chem. Commun., 2011, 47, 8322 DOI: 10.1039/C1CC12760H

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