Issue 55, 2012
From the journal:

Chemical Communications

Enantio- and diastereoselective hetero-Diels–Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates†‡

Yudai Watanabe,a   Takuya Washio,a   Janagiraman Krishnamurthi,a   Masahiro Anada*a  and  Shunichi Hashimoto*a  

* Corresponding authors

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

Abstract

The first catalytic asymmetric hetero-Diels–Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh2(S-BPTPI)4, the cycloaddition reaction proceeded exclusively in an endo mode to give all-cis-substituted 1,3-oxazinan-4-ones in high yields with up to 98% ee.

Graphical abstract: Enantio- and diastereoselective hetero-Diels–Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates

  • This article is part of the themed collection: Chirality
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Article information

DOI
https://doi.org/10.1039/C2CC32876C
Article type
Communication
Submitted
23 Apr 2012
Accepted
17 May 2012
First published
18 May 2012

Chem. Commun., 2012,48, 6969-6971

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Enantio- and diastereoselective hetero-Diels–Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(II) carboxamidates

Y. Watanabe, T. Washio, J. Krishnamurthi, M. Anada and S. Hashimoto, Chem. Commun., 2012, 48, 6969 DOI: 10.1039/C2CC32876C

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