Issue 22, 2011
From the journal:

Organic & Biomolecular Chemistry

Deuterium-isotope study on the reductive ring opening of benzylidene acetals†

I-Chi Lee,a   Medel Manuel L. Zulueta,ab   Chi-Rung Shie,a   Susan D. Arcob  and  Shang-Cheng Hung*ac  

* Corresponding authors

a Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei 115, Taiwan
E-mail: schung@gate.sinica.edu.tw

b Institute of Chemistry, University of the Philippines, Diliman, Quezon City 1101, Philippines

c Department of Applied Chemistry, National Chiao Tung University, 1001, Ta-Hsueh Road, Hsinchu, Taiwan

Abstract

Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD3 revealed a retentive stereoselectivity probably through the rare SNi (internal nucleophilic substitution) mechanism. An SN1-like mechanism occurs in the acid-promoted regioselective BD3·THF- or Et3SiD-reductive ring opening.

Graphical abstract: Deuterium-isotope study on the reductive ring opening of benzylidene acetals

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1OB06056B
Article type
Communication
Submitted
30 Jun 2011
Accepted
18 Aug 2011
First published
16 Sep 2011

Org. Biomol. Chem., 2011,9, 7655-7658

Permissions

Request permissions

Deuterium-isotope study on the reductive ring opening of benzylidene acetals

I. Lee, M. M. L. Zulueta, C. Shie, S. D. Arco and S. Hung, Org. Biomol. Chem., 2011, 9, 7655 DOI: 10.1039/C1OB06056B

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