Issue 58, 2015
From the journal:

Chemical Communications

A chiral phosphoric acid catalyst for asymmetric construction of 1,3-dioxanes†

Akira Matsumoto,a   Keisuke Asano*a  and  Seijiro Matsubara*a  

* Corresponding authors

a Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan
E-mail: asano.keisuke.5w@kyoto-u.ac.jp, matsubara.seijiro.2e@kyoto-u.ac.jp
Fax: +81 75 383 2438
Tel: +81 75 383 7571

Abstract

A novel method of enantioselective 1,3-dioxane construction via a hemiacetalization/intramolecular oxy-Michael addition cascade by a chiral phosphoric acid catalyst was developed. The product was successfully transformed into an optically active 1,3-polyol motif, indicating that the proposed reaction can provide useful chiral building blocks for the de novo synthesis of polyketides.

Graphical abstract: A chiral phosphoric acid catalyst for asymmetric construction of 1,3-dioxanes

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Article information

DOI
https://doi.org/10.1039/C5CC04124D
Article type
Communication
Submitted
19 May 2015
Accepted
09 Jun 2015
First published
12 Jun 2015

Chem. Commun., 2015,51, 11693-11696

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A chiral phosphoric acid catalyst for asymmetric construction of 1,3-dioxanes

A. Matsumoto, K. Asano and S. Matsubara, Chem. Commun., 2015, 51, 11693 DOI: 10.1039/C5CC04124D

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