Synthesis of 4-substituted tetrahydropyridines by cross-coupling of enol phosphates

被引:66
作者
Larsen, US
Martiny, L
Begtrup, M [1 ]
机构
[1] Danish Univ Pharmaceut Sci, Dept Med Chem, DK-2100 Copenhagen, Denmark
[2] Novo Nordisk AS, Isotope Chem, DK-2760 Malov, Denmark
[3] Riso Natl Lab, Radiat Res Dept, DK-4000 Roskilde, Denmark
关键词
D O I
10.1016/j.tetlet.2005.03.203
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enol phosphates, synthesized from 4-piperidone, react by palladium catalyzed cross-coupling with arylboronic acids and by iron and palladium catalyzed cross-coupling with Grignard reagents to give 4-substituted tetrahydropyridines. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4261 / 4263
页数:3
相关论文
共 31 条
[1]   Synthesis of 3-substituted-4H-1,4-benzoxazines via palladium-catalysed coupling reactions [J].
Buon, C ;
Bouyssou, P ;
Coudert, G .
TETRAHEDRON LETTERS, 1999, 40 (04) :701-702
[2]   Synthesis of 3-substituted and 2,3-disubstituted-4H-1,4-benzoxazines [J].
Buon, C ;
Chacun-Lefèvre, L ;
Rabot, R ;
Bouyssou, P ;
Coudert, G .
TETRAHEDRON, 2000, 56 (04) :605-614
[3]  
Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199
[4]   A simple solid phase diversity linker strategy using enol phosphonates [J].
Campbell, IB ;
Guo, J ;
Jones, E ;
Steel, PG .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) :2725-2727
[5]   Total synthesis of (±)-cytisine via the intramolecular heck cyclization of activated N-alkyl glutarimides [J].
Coe, JW .
ORGANIC LETTERS, 2000, 2 (26) :4205-4208
[6]  
Dohle W, 2001, SYNLETT, P1901
[7]  
Fürstner A, 2002, ANGEW CHEM INT EDIT, V41, P609
[8]   Total synthesis of (-)-gambierol [J].
Fuwa, H ;
Kainuma, N ;
Tachibana, K ;
Sasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14983-14992
[9]  
Huffman MA, 1999, SYNLETT, P471
[10]   Asymmetric synthesis of chiral, nonracemic trifluoromethyl-substituted piperidines and decahydroquinolines [J].
Jiang, JL ;
DeVita, RJ ;
Doss, GA ;
Goulet, MT ;
Wyvratt, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (03) :593-594