Synthsis of 4-Piperidones via Multicomponent Double Mannich Reaction Catalyzed by I2

A multicomponent double Mannich reaction of amines, aldehydes and ketones was efficiently catalyzed by molecular iodine, producing a series of 4-piperidones in a stereoselective way. A variety of amines, aldehydes and ketones were tolerated in this tandem process, including those with labile functin...

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Published inChinese journal of chemistry Vol. 30; no. 7; pp. 1504 - 1510
Main Author 贾晓东 陈向宁 霍聪德 彭芳芳 卿嫦 王喜存
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.07.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
4-piperidones
Chemistry
Chemistry, Multidisciplinary
double Mannich reaction
Iodine
Mannich反应
multicomponent reaction
Physical Sciences
Science & Technology
tandem cyclization
不稳定
催化合成
哌啶酮
多组分
碘分子
耐受性
胺类
tandem cyclization
double Mannich reaction
CHIRAL AMINO SULFONAMIDE
ACID
THIOUREA
ORGANOCATALYST
4-piperidones
CONSTRUCTION
iodine
multicomponent reaction
DERIVATIVES
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Summary:A multicomponent double Mannich reaction of amines, aldehydes and ketones was efficiently catalyzed by molecular iodine, producing a series of 4-piperidones in a stereoselective way. A variety of amines, aldehydes and ketones were tolerated in this tandem process, including those with labile functinal groups. Further investigation of the reaction between alkyl-imines and ketones showed that imines from amines and ketones were formed in situ and isomerized to enamine in the presence of molecular iodine to accelerate the corresponding Mannich addition.
Bibliography:A multicomponent double Mannich reaction of amines, aldehydes and ketones was efficiently catalyzed by molecular iodine, producing a series of 4-piperidones in a stereoselective way. A variety of amines, aldehydes and ketones were tolerated in this tandem process, including those with labile functinal groups. Further investigation of the reaction between alkyl-imines and ketones showed that imines from amines and ketones were formed in situ and isomerized to enamine in the presence of molecular iodine to accelerate the corresponding Mannich addition.
31-1547/O6
double Mannich reaction, multicomponent reaction, tandem cyclization, 4-piperidones, iodine
NSFC - No. 21002079
Project supported by the Ministry of Education of the People's Republic of China - No. 20096203120002
ArticleID:CJOC201100717
ark:/67375/WNG-2CGW1HG3-R
the third Knowledge and Technological Innovation Project of Northwest Normal University - No. NWNU-KJCXGC-03-75 and NWNU- KJCXGC-03-64
istex:95042494CB3DF69E6DF830506EE4D70AA0585EF3
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201100717