@article{2d232796d88b4707b33a3b2e912e47c6,
title = "Identification of Reactive Intermediates for the Decarbonylative Reaction of 1-Alkylprolines",
abstract = "1-Alkylprolines undergo decarbonylative reactions with oxalyl chloride and subsequent Mannich reactions with nonactivated C-H nucleophiles to give 2-substituted pyrrolidines as Mannich adducts. We showed that 1-alkyl-1-pyrrolinium compounds are the reactive intermediates formed by the decarbonylative reactions of 1-alkylprolines. Our results also confirmed that an azomethine ylide, although unreactive toward the Mannich reaction and not involved in the decarbonylative Mannich reaction, can be generated by deprotonation of the corresponding 1-alkyl-1-pyrrolinium compound under mild conditions.",
keywords = "azomethine ylides, electrophilic aromatic substitution, Mannich reaction, pyrrolidines, pyrrolinium compounds",
author = "Shih, {Yu Chiao} and Wang, {Jing Shiuan} and Hsu, {Chia Chun} and Tsai, {Pei Hua} and Chien, {Tun Cheng}",
note = "Funding Information: This work was supported by Research Grants 104-2113-M-003-001- and 103-2113-M-003-007- from the Ministry of Science and Technology, Taiwan. We also thank Professor Cheng-Huang Lin (National Taiwan Normal University) for his assistance with MS analyses Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart. New York.",
year = "2016",
month = dec,
day = "15",
doi = "10.1055/s-0036-1588593",
language = "English",
volume = "27",
pages = "2841--2845",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "20",
}