Issue 49, 2015
From the journal:

Chemical Communications

Regioselectivity switch in chiral amine-catalysed asymmetric addition of aldehydes to reactive enals†

Taichi Kano,a   Hiroki Maruyama,a   Ryu Sakamotoa  and  Keiji Maruoka*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
E-mail: maruoka@kuchem.kyoto-u.ac.jp

Abstract

In this communication, we present a regioselectivity switch for the chiral amine-catalysed asymmetric addition of aldehydes to reactive enals to afford either aldol adducts or conjugate adducts in a stereoselective fashion. The unprecedented asymmetric aldol reaction of aldehydes with enals was realized by the use of a diarylprolinol catalyst, giving synthetically useful and important chiral allylic alcohols.

Graphical abstract: Regioselectivity switch in chiral amine-catalysed asymmetric addition of aldehydes to reactive enals

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Article information

DOI
https://doi.org/10.1039/C5CC02438B
Article type
Communication
Submitted
22 Apr 2015
Accepted
12 May 2015
First published
12 May 2015

Chem. Commun., 2015,51, 10062-10065

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Regioselectivity switch in chiral amine-catalysed asymmetric addition of aldehydes to reactive enals

T. Kano, H. Maruyama, R. Sakamoto and K. Maruoka, Chem. Commun., 2015, 51, 10062 DOI: 10.1039/C5CC02438B

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