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

11 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

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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, MCP, 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 MCP, 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.
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