Cascade Synthesis of Fenpiprane and Related Pharmaceuticals via Rhodium-Catalyzed Hydroaminomethylation

被引:35
作者
Li, Shengkun [1 ,2 ,3 ]
Huang, Kexuan [2 ,3 ]
Zhang, Jiwen [1 ]
Wu, Wenjun [1 ]
Zhang, Xumu [2 ,3 ]
机构
[1] Northwest A&F Univ, Coll Sci, Yangling 712100, Shaanxi, Peoples R China
[2] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
[3] Rutgers State Univ, Dept Pharmaceut Chem, Piscataway, NJ 08854 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
HIGHLY REGIOSELECTIVE HYDROFORMYLATION; INTERNAL OLEFINS; ISOMERIZATION-HYDROFORMYLATION; DICATIONIC ELECTROPHILES; COMPLEXES; LIGANDS; AMINES;
D O I
10.1021/ol303483t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel rhodium catalytic system with Naphos as ligand was developed for an efficient hydroaminomethylation of 1,1-diphenylethene under relatively mild conditions. This will allow for an atom-economic and environmentally benign synthesis of fenpiprane and related pharmaceuticals.
引用
收藏
页码:1036 / 1039
页数:4
相关论文
共 37 条
[1]   Amines made easily: A highly selective hydroaminomethylation of olefins [J].
Ahmed, M ;
Seayad, AM ;
Jackstell, R ;
Beller, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10311-10318
[2]   Hydroaminomethylation with novel rhodium-carbene complexes: An efficient catalytic approach to pharmaceuticals [J].
Ahmed, Moballigh ;
Buch, Cathleen ;
Routaboul, Lucie ;
Jackstell, Ralf ;
Klein, Holger ;
Spannenberg, Anke ;
Beller, Matthias .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) :1594-1601
[3]   Asymmetric total synthesis of (+)-tolterodine, a new muscarinic receptor antagonist, via copper-assisted asymmetric conjugate addition of aryl Grignard reagents to 3-phenyl-prop-2-enoyl-oxazolidinones [J].
Andersson, PG ;
Schink, HE ;
Österlund, K .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :8067-8070
[4]  
[Anonymous], SURVEY IND CHEM
[5]  
[Anonymous], 1992, APPL ORGANOMET CHEM
[6]   NEW SYNTHETIC ROUTE TO PHARMACOLOGICALLY ACTIVE 1-(N,N-DIALKYLAMINO)-3,3-DIARYLPROPANES VIA RHODIUM-CATALYZED HYDROFORMYLATION OF 1,1-DIARYLETHENES [J].
BOTTEGHI, C ;
CAZZOLATO, L ;
MARCHETTI, M ;
PAGANELLI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6612-6615
[7]   Modulators of the human CCR5 receptor. Part 1: Discovery and initial SAR of 1-(3,3-diphenylpropyl)-piperidinyl amides and ureas [J].
Burrows, JN ;
Cumming, JG ;
Fillery, SM ;
Hamlin, GA ;
Hudson, JA ;
Jackson, RJ ;
McLaughlin, S ;
Shaw, JS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (01) :25-28
[8]   New Tetraphosphorus Ligands for Highly Linear Selective Hydroformylation of Allyl and Vinyl Derivatives [J].
Cai, Chaoxian ;
Yu, Shichao ;
Cao, Bonan ;
Zhang, Xumu .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (32) :9992-9998
[9]  
Certa H., 1990, ARCH PHARM, V323, P744
[10]   Recent Advances in Amine Synthesis by Catalytic Hydroaminomethylation of Alkenes [J].
Crozet, Delphine ;
Urrutigoity, Martine ;
Kalck, Philippe .
CHEMCATCHEM, 2011, 3 (07) :1102-1118