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I 2 ‐Induced Stereospecific Synthesis of 4‐Piperidones through Double Mannich Reaction and Tandem Cyclization
Author(s) -
Jia XiaoDong,
Chen XiangNing,
Wang XiaoE,
Huo CongDe,
Wang WenJuan,
Ren Yan,
Wang XiCun
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001607
Subject(s) - chemistry , mannich reaction , stereospecificity , tandem , double bond , cascade reaction , combinatorial chemistry , reaction conditions , stereochemistry , organic chemistry , medicinal chemistry , catalysis , materials science , composite material
An I 2 ‐induced double Mannich reaction and tandem cyclization of imines and ketones was investigated for the synthesis of a series of 1,2,6‐triaryl‐4‐piperidones. During the process of cyclization, only one product was produced out of four possible 4‐piperidones. Two pathways involving the balance between chelation effects and hydrogen bonding were proposed to rationalize the formation of the products, which was supported by further investigation of the reaction between β‐aminoketones and imines.