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 | |
| Publication status | Published - 2012 Apr 6 |
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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 journal › Article
}
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 -