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

Access to Document

10.1021/acs.orglett.6b00916

Fingerprint Dive into the research topics of 'Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams'. Together they form a unique fingerprint.

Cite this

@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}",

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. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

year = "2016",

month = may,

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

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. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

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

AN - SCOPUS:84971222202

VL - 18

SP - 2407

EP - 2410

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -