Abstract
An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 2196-2201 |
| Number of pages | 6 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 359 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 2017 Jan 1 |
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Keywords
- Lewis acids
- amides
- amines
- cyclization
- diastereoselectivity
- halogenation
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides. / Yeh, Ming-Chang P.; Chang, Yi Mei; Lin, Hsin Hui.
In: Advanced Synthesis and Catalysis, Vol. 359, No. 13, 01.01.2017, p. 2196-2201.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides
AU - Yeh, Ming-Chang P.
AU - Chang, Yi Mei
AU - Lin, Hsin Hui
PY - 2017/1/1
Y1 - 2017/1/1
N2 - An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).
AB - An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).
KW - Lewis acids
KW - amides
KW - amines
KW - cyclization
KW - diastereoselectivity
KW - halogenation
UR - http://www.scopus.com/inward/record.url?scp=85018994155&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85018994155&partnerID=8YFLogxK
U2 - 10.1002/adsc.201700271
DO - 10.1002/adsc.201700271
M3 - Article
VL - 359
SP - 2196
EP - 2201
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 13
ER -