One-pot three-component reaction for the synthesis of α-(aminoethyl)-α,β-enones

被引:38
作者
Bertozzi, F [1 ]
Gustafsson, M [1 ]
Olsson, R [1 ]
机构
[1] ACADIA Pharmaceut AS, Discovery Chem, DK-2600 Glostrup, Denmark
关键词
D O I
10.1021/ol026976t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic The synthesis of alpha-substituted alpha,beta-enones by a new metal iodide-promoted one-pot three-component reaction involving commercially available cyclopropyl ketones, aldehydes, and secondary amines followed by base treatment is described.
引用
收藏
页码:4333 / 4336
页数:4
相关论文
共 39 条
[1]   Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain [J].
Adger, BM ;
Barkley, JV ;
Bergeron, S ;
Cappi, MW ;
Flowerdew, BE ;
Jackson, MP ;
McCague, R ;
Nugent, TC ;
Roberts, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23) :3501-3507
[2]  
Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
[3]  
2-5
[4]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[5]   Parallel solution phase synthesis of N-substituted 2-pyrazoline libraries [J].
Bauer, U ;
Egner, BJ ;
Nilsson, I ;
Berghult, M .
TETRAHEDRON LETTERS, 2000, 41 (15) :2713-2717
[6]   Highly enantioselective enone epoxidation catalyzed by short solid phase-bound peptides: Dominant role of peptide helicity [J].
Berkessel, A ;
Gasch, N ;
Glaubitz, K ;
Koch, C .
ORGANIC LETTERS, 2001, 3 (24) :3839-3842
[7]   A novel metal iodide promoted three-component synthesis of substituted pyrrolidines [J].
Bertozzi, F ;
Gustafsson, M ;
Olsson, R .
ORGANIC LETTERS, 2002, 4 (18) :3147-3150
[8]  
Biginelli P., 1891, BERICHTE DTSCH CHEM, V24, P1317, DOI [DOI 10.1002/CBER.189102401228, 10.1002/cber.189102401228]
[9]   Synthesis of tertiary amines using a polystyrene (REM) resin [J].
Brown, AR ;
Rees, DC ;
Rankovic, Z ;
Morphy, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3288-3295
[10]   ELECTROPHILIC CYCLOPROPANES IN ORGANIC-SYNTHESIS [J].
DANISHEFSKY, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (02) :66-72