Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

Ming Chang P. Yeh; Cheng Wei Fang; Hsin Hui Lin

doi:10.1021/ol300434m

Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

Ming Chang P. Yeh, Cheng Wei Fang, Hsin Hui Lin

Department of Chemistry

Research output: Contribution to journal › Article

22 Citations (Scopus)

Abstract

A simple and efficient FeCl ₃-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 °C in air to afford (Z)-4- (arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl ₃.

Original language	English
Pages (from-to)	1830-1833
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	7
DOIs	https://doi.org/10.1021/ol300434m
Publication status	Published - 2012 Apr 6

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Yeh, M. C. P., Fang, C. W., & Lin, H. H. (2012). Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols. Organic Letters, 14(7), 1830-1833. https://doi.org/10.1021/ol300434m

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abstract = "A simple and efficient FeCl 3-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 °C in air to afford (Z)-4- (arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl 3.",

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10.1021/ol300434m