Issue 47, 2009

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

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

Supplementary files

Article information

Article type
Communication
Submitted
18 Sep 2009
Accepted
05 Okt 2009
First published
15 Okt 2009

Chem. Commun., 2009, 7294-7296

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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