Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides

Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams

Ming-Chang P. Yeh, Yuan Shin Shiue, Hsin Hui Lin, Tzu Yu Yu, Ting Chia Hu, Jia Jyun Hong

Research output: Contribution to journal › Article

9 Citations (Scopus)

Abstract

A simple and mild process was developed for the highly stereoselective synthesis of halogenated bicyclic [4.3.0] and [3.3.0] γ-lactams, possessing four stereocenters, from easily available cyclic 2-enynamides. The reaction required only an inexpensive iron(II) halide under dry air and was tolerant of aryl, heteroaryl, and alkyl groups at the alkyne terminus.

Original languageEnglish
Pages (from-to)2407-2410
Number of pages4
JournalOrganic Letters
Volume18
Issue number10
DOIs
Publication statusPublished - 2016 May 20

Fingerprint

Lactams
Alkynes
Cyclization
alkynes
halides
Iron
Air
iron
air
synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides : Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams. / Yeh, Ming-Chang P.; Shiue, Yuan Shin; Lin, Hsin Hui; Yu, Tzu Yu; Hu, Ting Chia; Hong, Jia Jyun.

In: Organic Letters, Vol. 18, No. 10, 20.05.2016, p. 2407-2410.

Research output: Contribution to journal › Article

Yeh, M-CP, Shiue, YS, Lin, HH, Yu, TY, Hu, TC & Hong, JJ 2016, 'Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams', Organic Letters, vol. 18, no. 10, pp. 2407-2410. https://doi.org/10.1021/acs.orglett.6b00916
Yeh M-CP, Shiue YS, Lin HH, Yu TY, Hu TC, Hong JJ. Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams. Organic Letters. 2016 May 20;18(10):2407-2410. https://doi.org/10.1021/acs.orglett.6b00916
Yeh, Ming-Chang P. ; Shiue, Yuan Shin ; Lin, Hsin Hui ; Yu, Tzu Yu ; Hu, Ting Chia ; Hong, Jia Jyun. / Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides : Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams. In: Organic Letters. 2016 ; Vol. 18, No. 10. pp. 2407-2410.
@article{88e5dad7354644d1b0cfad44b6d1e831,
title = "Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams",
abstract = "A simple and mild process was developed for the highly stereoselective synthesis of halogenated bicyclic [4.3.0] and [3.3.0] γ-lactams, possessing four stereocenters, from easily available cyclic 2-enynamides. The reaction required only an inexpensive iron(II) halide under dry air and was tolerant of aryl, heteroaryl, and alkyl groups at the alkyne terminus.",
author = "Yeh, {Ming-Chang P.} and Shiue, {Yuan Shin} and Lin, {Hsin Hui} and Yu, {Tzu Yu} and Hu, {Ting Chia} and Hong, {Jia Jyun}",
year = "2016",
month = "5",
day = "20",
doi = "10.1021/acs.orglett.6b00916",
language = "English",
volume = "18",
pages = "2407--2410",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides

T2 - Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams

AU - Yeh, Ming-Chang P.

AU - Shiue, Yuan Shin

AU - Lin, Hsin Hui

AU - Yu, Tzu Yu

AU - Hu, Ting Chia

AU - Hong, Jia Jyun

PY - 2016/5/20

Y1 - 2016/5/20

N2 - A simple and mild process was developed for the highly stereoselective synthesis of halogenated bicyclic [4.3.0] and [3.3.0] γ-lactams, possessing four stereocenters, from easily available cyclic 2-enynamides. The reaction required only an inexpensive iron(II) halide under dry air and was tolerant of aryl, heteroaryl, and alkyl groups at the alkyne terminus.

AB - A simple and mild process was developed for the highly stereoselective synthesis of halogenated bicyclic [4.3.0] and [3.3.0] γ-lactams, possessing four stereocenters, from easily available cyclic 2-enynamides. The reaction required only an inexpensive iron(II) halide under dry air and was tolerant of aryl, heteroaryl, and alkyl groups at the alkyne terminus.

UR - http://www.scopus.com/inward/record.url?scp=84971222202&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84971222202&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b00916

DO - 10.1021/acs.orglett.6b00916

M3 - Article

VL - 18

SP - 2407

EP - 2410

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -

Access to Document