Indium(III)-Catalyzed Asymmetric Hetero-Diels–Alder Reaction of Brassard-Type Diene with Aliphatic Aldehydes

A highly diastereo- and enantioselective hetero-Diels–Alder (HDA) reaction of a Brassard-type diene with aliphatic aldehydes has been developed. The chiral N,N′-dioxide L2/In(OTf)3 complex was efficient toward the obtention of the corresponding β-methoxy-γ-methyl α,β-unsaturated δ-lactones in good y...

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Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (15), p.3868-3871
Main Authors: Lin, Lili, Kuang, Yulong, Liu, Xiaohua, Feng, Xiaoming
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Catalysis
Hydrogenation
Indium - chemistry
Ligands
Molecular Structure
Stereoisomerism
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Summary:A highly diastereo- and enantioselective hetero-Diels–Alder (HDA) reaction of a Brassard-type diene with aliphatic aldehydes has been developed. The chiral N,N′-dioxide L2/In(OTf)3 complex was efficient toward the obtention of the corresponding β-methoxy-γ-methyl α,β-unsaturated δ-lactones in good yields (up to 86%) as well as dr and ee values (up to 97:3 cis/trans and 94% ee). In addition, the product 4a could be easily transformed into the methyl-protected epi-prelactone B by hydrogenation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2013999