Stereoselective three-component synthesis of trans-endo-decahydroquinolin-4-one derivatives from aldehydes, aniline, and acetylcyclohexene.
The diastereoselective synthesis of trans-endo-decahydroquinolin-4-one (4) via a three-component reaction of aldehydes (1), anilines (2), and 1-acetylcyclohexene (3) in the presence of iodine in a one-pot reaction at room temperature is described. The short reaction time, easy workup, excellent yield, and mild reaction conditions make this novel annulation strategy both practical and attractive.
Lin
Chunchi
C
Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei, Taiwan 116, Republic of China.
Fang
Hulin
H
Tu
Zhijay
Z
Liu
Ju-Tsung
JT
Yao
Ching-Fa
CF
D000447:Aldehydes / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D053138:Cyclohexenes / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000814:Aniline Compounds; D053138:Cyclohexenes; D015363:Quinolones; C520380:acetylcyclohexene; C023650:aniline