Brønsted Acid Catalyzed Asymmetric Diels–Alder Reactions: Stereoselective Construction of Spiro[tetrahydrocarbazole-3,3′-oxindole] Framework

The chiral phosphoric acid catalyzed asymmetric Diels–Alder reactions of 2-vinylindoles with methyleneindolinones have been established, which efficiently construct the spiro­[tetrahydro­carbazole-3,3′-oxindole] architecture with one quaternary and three contiguous stereogenic centers in high yields...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-03, Vol.80 (6), p.3223-3232
Main Authors: Wang, Yang, Tu, Man-Su, Yin, Lei, Sun, Meng, Shi, Feng
Format: Article
Language:English
Subjects:
Catalysis
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Phosphoric Acids - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:The chiral phosphoric acid catalyzed asymmetric Diels–Alder reactions of 2-vinylindoles with methyleneindolinones have been established, which efficiently construct the spiro­[tetrahydro­carbazole-3,3′-oxindole] architecture with one quaternary and three contiguous stereogenic centers in high yields (up to 99%) and excellent stereoselectivities (up to >95:5 dr, 97% ee). This reaction not only provides an efficient strategy to access enantioenriched spiro­[tetrahydro­carbazole-3,3′-oxindoles] based on hydrogen-bonding activation mode but also supplies successful examples of catalytic asymmetric Diels–Alder reactions for constructing complex spiro-frameworks with optical purity.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00198