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

^*Corresponding author for this work

Department of Chemistry

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

16 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

Cite this

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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 = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = may,

day = "20",

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

language = "English",

volume = "18",

pages = "2407--2410",

journal = "Organic Letters",

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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 - https://www.scopus.com/pages/publications/84971222202

UR - https://www.scopus.com/pages/publications/84971222202#tab=citedBy

U2 - 10.1021/acs.orglett.6b00916

DO - 10.1021/acs.orglett.6b00916

M3 - Article

AN - SCOPUS:84971222202

SN - 1523-7060

VL - 18

SP - 2407

EP - 2410

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

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

Abstract

ASJC Scopus subject areas

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CCDC 1444919: Experimental Crystal Structure Determination

CCDC 1448871: Experimental Crystal Structure Determination

CCDC 1421207: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 1444919: Experimental Crystal Structure Determination

CCDC 1448871: Experimental Crystal Structure Determination

CCDC 1421207: Experimental Crystal Structure Determination

Cite this