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

Yudai Watanabe; Takuya Washio; Naoyuki Shimada; Masahiro Anada; Shunichi Hashimoto

doi:10.1039/B919535A

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Chemical Communications

Issue 47, 2009

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

Yudai Watanabe , Takuya Washio , Naoyuki Shimada , Masahiro Anada and Shunichi Hashimoto

Chem. Commun., 2009, 7294-7296

DOI: 10.1039/B919535A
Received 18 Sep 2009, Accepted 05 Oct 2009
First published on the web 15 Oct 2009
This article is part of the collection: Selective Catalysis for Organic Synthesis

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Abstract
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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.

Abstract from Catalysts & Catalysed Reactions 2010

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Abstract from Methods in Organic Synthesis 2010

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Yudai Watanabe
Takuya Washio
Naoyuki Shimada
Masahiro Anada
Shunichi Hashimoto

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Chemical Communications

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

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