One-pot asymmetric synthesis of substituted piperidines by exocyclic chirality induction.
A highly efficient one-pot synthesis of substituted piperidines was developed through nitroalkene, amine, and enone condensation. The transformation was suitable for a large group of substrates, giving excellent yields and diastereoselectivity. Reactions using chiral amines revealed a chirality induction through the unusual exocyclic stereochemistry control, producing enantiomeric pure piperidines in simple steps.
Chen
Yunfeng
Y
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Zhong
Cheng
C
Petersen
Jeffrey L
JL
Akhmedov
Novruz G
NG
Shi
Xiaodong
X
D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000588:Amines; D007659:Ketones; D010880:Piperidines