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

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

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Yeh, M. C. P., Shiue, Y. S., Lin, H. H., Yu, T. Y., Hu, T. C., & Hong, J. J. (2016). Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams. Organic Letters, 18(10), 2407-2410. https://doi.org/10.1021/acs.orglett.6b00916

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AU - Hu, Ting Chia

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10.1021/acs.orglett.6b00916