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

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

15 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	2407-2410
頁數	4
期刊	Organic Letters
卷	18
發行號	10
DOIs	https://doi.org/10.1021/acs.orglett.6b00916
出版狀態	已發佈 - 2016 5月 20

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

存取文件

10.1021/acs.orglett.6b00916

其它文件與鏈接

CCDC 1421206: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Shiue, Y.-S. (Creator), Lin, H.-H. (Creator), Yu, T.-Y. (Creator), Hu, T.-C. (Creator) & Hong, J.-J. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1jpwcg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1jpwcg&sid=DataCite
資料集: Dataset
CCDC 1448870: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Shiue, Y.-S. (Creator), Lin, H.-H. (Creator), Yu, T.-Y. (Creator), Hu, T.-C. (Creator) & Hong, J.-J. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1kmnrl, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1kmnrl&sid=DataCite
資料集: Dataset
CCDC 1448871: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Shiue, Y.-S. (Creator), Lin, H.-H. (Creator), Yu, T.-Y. (Creator), Hu, T.-C. (Creator) & Hong, J.-J. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1kmnsm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1kmnsm&sid=DataCite
資料集: Dataset

引用此

@article{e9b4fd2ab92a4e12a844eaa3fc2c8b20,

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",

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

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1421206: Experimental Crystal Structure Determination

CCDC 1448870: Experimental Crystal Structure Determination

CCDC 1448871: Experimental Crystal Structure Determination

引用此