Identification of Reactive Intermediates for the Decarbonylative Reaction of 1-Alkylprolines

Yu Chiao Shih, Jing Shiuan Wang, Chia Chun Hsu, Pei Hua Tsai, Tun-Cheng Chien

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.

Original languageEnglish
Article numberst-2016-u0387-l
Pages (from-to)2841-2845
Number of pages5
JournalSynlett
Volume27
Issue number20
DOIs
Publication statusPublished - 2016 Dec 15

Fingerprint

Pyrrolidines
Deprotonation
Nucleophiles
oxalyl chloride
azomethine

Keywords

  • Mannich reaction
  • azomethine ylides
  • electrophilic aromatic substitution
  • pyrrolidines
  • pyrrolinium compounds

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Identification of Reactive Intermediates for the Decarbonylative Reaction of 1-Alkylprolines. / Shih, Yu Chiao; Wang, Jing Shiuan; Hsu, Chia Chun; Tsai, Pei Hua; Chien, Tun-Cheng.

In: Synlett, Vol. 27, No. 20, st-2016-u0387-l, 15.12.2016, p. 2841-2845.

Research output: Contribution to journalArticle

Shih, Yu Chiao ; Wang, Jing Shiuan ; Hsu, Chia Chun ; Tsai, Pei Hua ; Chien, Tun-Cheng. / Identification of Reactive Intermediates for the Decarbonylative Reaction of 1-Alkylprolines. In: Synlett. 2016 ; Vol. 27, No. 20. pp. 2841-2845.
@article{3e9a4dd8416648f3a1161f7055a3cf26,
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 = "Mannich reaction, azomethine ylides, electrophilic aromatic substitution, pyrrolidines, pyrrolinium compounds",
author = "Shih, {Yu Chiao} and Wang, {Jing Shiuan} and Hsu, {Chia Chun} and Tsai, {Pei Hua} and Tun-Cheng Chien",
year = "2016",
month = "12",
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",

}

TY - JOUR

T1 - Identification of Reactive Intermediates for the Decarbonylative Reaction of 1-Alkylprolines

AU - Shih, Yu Chiao

AU - Wang, Jing Shiuan

AU - Hsu, Chia Chun

AU - Tsai, Pei Hua

AU - Chien, Tun-Cheng

PY - 2016/12/15

Y1 - 2016/12/15

N2 - 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.

AB - 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.

KW - Mannich reaction

KW - azomethine ylides

KW - electrophilic aromatic substitution

KW - pyrrolidines

KW - pyrrolinium compounds

UR - http://www.scopus.com/inward/record.url?scp=84988311241&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84988311241&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1588593

DO - 10.1055/s-0036-1588593

M3 - Article

VL - 27

SP - 2841

EP - 2845

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 20

M1 - st-2016-u0387-l

ER -