One-pot synthesis of optically enriched 2-piperidinones from aliphatic aldehydes and cyanoacrylamides.
A highly stereoselective one-pot reaction of aliphatic aldehydes and cyanoacrylamides has been developed. The one-pot reaction includes an organocatalytic Michael addition followed by an intramolecular hemiaminalization. After reduction, optically enriched 2-piperidinones with three contiguous chiral centers were obtained in up to 95% yield and 9:1 dr with 99% ee.
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, 637009, China.
Ying
Y
He
Tai-Ran
TR
Kang
Quan-Zhong
QZ
Liu
Lian-Mei
LM
Chen
Yi-Lian
YL
Tu
Ya-Jun
YJ
Liu
Tang-Bin
TB
Chen
Zhi-Qiang
ZQ
Wang
Jie
J
Liu
Yong-Mei
YM
Xie
Jin-Liang
JL
Yang
Long
L
He
D000178:Acrylamides / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000178:Acrylamides; D000447:Aldehydes; D009570:Nitriles; D010881:Piperidones; C043384:2-piperidone