L‑Pyroglutamic Sulphonamide as Hydrogen-Bonding Organocatalyst: Enantioselective Diels–Alder Cyclization to Construct Carbazolespirooxindoles

Hydrogen-bonding organocatalysts L-pyroglutamic sulphonamides were readily synthesized for the first time by fully exploiting the potentials of L-pyroglutamic acid. The newly designed catalyst was successfully applied in catalyzing asymmetric Diels–Alder cyclization of methyleneindolinones with 2-vi...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-06, Vol.82 (12), p.6441-6449
Main Authors: Ren, Ji-Wei, Wang, Jing, Xiao, Jun-An, Li, Jun, Xiang, Hao-Yue, Chen, Xiao-Qing, Yang, Hua
Format: Article
Language:English
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Summary:Hydrogen-bonding organocatalysts L-pyroglutamic sulphonamides were readily synthesized for the first time by fully exploiting the potentials of L-pyroglutamic acid. The newly designed catalyst was successfully applied in catalyzing asymmetric Diels–Alder cyclization of methyleneindolinones with 2-vinyl-1H-indoles to efficiently assemble carbazolespirooxindoles in excellent stereoselectivity (up to 99% ee, >20:1 dr) and yields (up to 99%). Mechanistic studies disclosed that the well-designed hydrogen-bonding modes between L-pyroglutamic sulphonamide and substrates were crucial for stereocontrol in the cyclization.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00733