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Issue 47, 2010

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

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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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Publication details

The article was received on 18 Sep 2009, accepted on 05 Oct 2009 and first published on 15 Oct 2009


Article type: Communication
DOI: 10.1039/B919535A
Citation: Chem. Commun., 2010,0, 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., 2010, 0, 7294
    DOI: 10.1039/B919535A

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