Aminohydroxylation and dihydroxylation of 4-aryl-1,2,5,6-tetrahydropyridines

被引:7
作者
Chang, Meng-Yang [1 ]
Lin, Chun-Yu
Wu, Tsun-Cheng
机构
[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan
[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
关键词
cerium ammonium nitrate; oxidative addition; hydrogenation; 4-aryl-1,2,5,6-tetrahydropyridines; aminohydroxylation; dihydroxylation;
D O I
10.1016/j.tetlet.2006.05.174
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted 3-amino-4-aryl-4-liydi-oxypiperidines and 4-aryl-3.4-dihvdroxypiperidiiies are synthesized in the modest overall yields starting from the regio- and stereoselective trans-aminohydroxylation and dihydroxylation of 4-aryl-1,15.6-tetrahydropyridines via CAN-mediated oxidative addition and hydrogenation. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5445 / 5449
页数:5
相关论文
共 72 条
[1]   Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine [J].
Amat, M ;
Bosch, J ;
Hidalgo, J ;
Cantó, M ;
Pérez, M ;
Llor, N ;
Molins, E ;
Miravitlles, C ;
Orozco, M ;
Luque, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3074-3084
[2]  
ANGCIT H, 1996, ANGEW CHEM INT EDIT, V35, P2813
[3]   Remarkably efficient deprotection of cyclic acetals and ketals [J].
Ates, A ;
Gautier, A ;
Leroy, B ;
Plancher, JM ;
Quesnel, Y ;
Markó, IE .
TETRAHEDRON LETTERS, 1999, 40 (09) :1799-1802
[4]   The Sharpless asymmetric aminohydroxylation [J].
Bodkin, JA ;
McLeod, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24) :2733-2746
[5]  
BOLM C, 2000, CATALYTIC ASYMMETRIC, P398
[6]   N-bromoacetamide - A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins [J].
Bruncko, M ;
Schlingloff, G ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1483-1486
[7]   Chemoselective oxidative debenzylation of tertiary N-benzyl amines [J].
Bull, SD ;
Davies, SG ;
Fenton, G ;
Mulvaney, AW ;
Prasad, RS ;
Smith, AD .
CHEMICAL COMMUNICATIONS, 2000, (05) :337-338
[8]  
Chakrabarty M., 1996, SYNTHETIC COMMUN, V24, P1
[9]   New synthesis of cis-3,4-diaryl-1-tosylpyrrolidines [J].
Chang, Meng-Yang ;
Pai, Chun-Li ;
Lin, Chun-Yu .
TETRAHEDRON LETTERS, 2006, 47 (22) :3641-3644
[10]   CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines [J].
Chang, MY ;
Lin, CY ;
Pai, CL .
TETRAHEDRON LETTERS, 2006, 47 (15) :2565-2568