Issue 47, 2010
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

About
Cited by
Related
Download options Please wait...

Supplementary files

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., 2010, 7294-7296

Permissions

Request permissions

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., 2010, 7294 DOI: 10.1039/B919535A

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