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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)1830-1833
Number of pages4
JournalOrganic Letters
Volume14
Issue number7
DOIs
Publication statusPublished - 2012 Apr 6

Fingerprint

chlorination
Chlorination
Halogenation
Cyclization
Iron
chlorides
Air
analogs
iron
air
synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols. / Yeh, Ming Chang P.; Fang, Cheng Wei; Lin, Hsin Hui.

In: Organic Letters, Vol. 14, No. 7, 06.04.2012, p. 1830-1833.

Research output: Contribution to journalArticle

@article{be233607873e4ef3ae2fb380b5a91a35,
title = "Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols",
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.",
author = "Yeh, {Ming Chang P.} and Fang, {Cheng Wei} and Lin, {Hsin Hui}",
year = "2012",
month = "4",
day = "6",
doi = "10.1021/ol300434m",
language = "English",
volume = "14",
pages = "1830--1833",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "7",

}

TY - JOUR

T1 - Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

AU - Yeh, Ming Chang P.

AU - Fang, Cheng Wei

AU - Lin, Hsin Hui

PY - 2012/4/6

Y1 - 2012/4/6

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84859613811&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84859613811&partnerID=8YFLogxK

U2 - 10.1021/ol300434m

DO - 10.1021/ol300434m

M3 - Article

C2 - 22455465

AN - SCOPUS:84859613811

VL - 14

SP - 1830

EP - 1833

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 7

ER -