Asymmetric Diels–Alder Reaction of 2‑Methyl-3-indolylmethanols via in Situ Generation of o‑Quinodimethanes

An asymmetric Diels–Alder reaction of 2-methyl-3-indolylmethanols and α,β-unsaturated aldehydes has been developed that relies on in situ generation of active indole-2,3-quinodimethane intermediates under mild acidic conditions and uses a secondary chiral amine as iminium activation catalyst. An arr...

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Bibliographic Details
Published in:Organic letters 2012-12, Vol.14 (23), p.5940-5943
Main Authors: Xiao, You-Cai, Zhou, Qing-Qing, Dong, Lin, Liu, Tian-Yu, Chen, Ying-Chun
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Carbazoles - chemical synthesis
Carbazoles - chemistry
Catalysis
Crystallography, X-Ray
Heterocyclic Compounds, 2-Ring - chemistry
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Indoles - chemistry
Molecular Conformation
Molecular Structure
Stereoisomerism
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Summary:An asymmetric Diels–Alder reaction of 2-methyl-3-indolylmethanols and α,β-unsaturated aldehydes has been developed that relies on in situ generation of active indole-2,3-quinodimethane intermediates under mild acidic conditions and uses a secondary chiral amine as iminium activation catalyst. An array of highly enantioenriched tetrahydrocarbazoles have been efficiently produced in fair to good yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302853m