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

doi:10.1021/acs.orglett.6b00916

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

12 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 language	English
Pages (from-to)	2407-2410
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.6b00916
Publication status	Published - 2016 May 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b00916

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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}",

note = "Funding Information: We thank the Ministry of Science and Technology of the Republic of China (MOST 104-2113-M-003-003) for financial support. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = may,

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doi = "10.1021/acs.orglett.6b00916",

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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

N1 - Funding Information: We thank the Ministry of Science and Technology of the Republic of China (MOST 104-2113-M-003-003) for financial support. Publisher Copyright: © 2016 American Chemical Society.

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.

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Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams

Abstract

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