Issue 47, 2009
From the journal:

Chemical Communications

Highly enantioselective hetero-Diels–Alder reactions between Rawal’s diene and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates†‡

Yudai Watanabe,a   Takuya Washio,a   Naoyuki Shimada,a   Masahiro Anadaa  and  Shunichi Hashimoto*a  

* Corresponding authors

a Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan
E-mail: hsmt@pharm.hokduai.ac.jp
Fax: +81 11 706 4981
Tel: +81 11 706 3236

Abstract

The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels–Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3-butadiene (Rawal’s diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol% of dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh2(S-BPTPI)4, proceeded cleanly and gave, after treatment with acetyl chloride, the corresponding dihydropyranones in up to 99% ee.

Graphical abstract: Highly enantioselective hetero-Diels–Alder reactions between Rawal’s diene and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates

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Article information

DOI
https://doi.org/10.1039/B919535A
Article type
Communication
Submitted
18 Sep 2009
Accepted
05 Oct 2009
First published
15 Oct 2009

Chem. Commun., 2009, 7294-7296

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Highly enantioselective hetero-Diels–Alder reactions between Rawal’s diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates

Y. Watanabe, T. Washio, N. Shimada, M. Anada and S. Hashimoto, Chem. Commun., 2009, 7294 DOI: 10.1039/B919535A

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