Issue 12, 2011
From the journal:

Organic & Biomolecular Chemistry

Asymmetric alkynylation of aldehydes with propiolates without high reagent loading and any additives†

Naoto Kojima,*a   Shogo Nishijima,a   Kaoru Tsugea  and  Tetsuaki Tanaka*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0879, Japan
E-mail: kojima@phs.osaka-u.ac.jp, t-tanaka@phs.osaka-u.ac.jp
Fax: +81-6-6879-8214
Tel: +81-6-6879-8210

Abstract

The asymmetric alkynylation of aliphatic and aromatic aldehydes with propiolates was mediated by dialkylzinc and a novel prolinol catalyst without high reagent loading and any additives, such as Ti(Oi-Pr)4, to give the corresponding γ-hydroxy-α,β-acetylenic esters with high enantiomeric excess of up to 95%.

Graphical abstract: Asymmetric alkynylation of aldehydes with propiolates without high reagent loading and any additives

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Article information

DOI
https://doi.org/10.1039/C1OB05489A
Article type
Communication
Submitted
29 Mar 2011
Accepted
20 Apr 2011
First published
21 Apr 2011

Org. Biomol. Chem., 2011,9, 4425-4428

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Asymmetric alkynylation of aldehydes with propiolates without high reagent loading and any additives

N. Kojima, S. Nishijima, K. Tsuge and T. Tanaka, Org. Biomol. Chem., 2011, 9, 4425 DOI: 10.1039/C1OB05489A

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