A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas

被引:65
作者
Fritz, Jonathan A. [1 ]
Nakhla, Josephine S. [1 ]
Wolfe, John P. [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/ol060707b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the preparation of substituted imidazolidin-2-ones in two steps from readily available N-allylamines is described. Addition of the amine starting materials to isocyanates affords N-allylureas, which are converted to imidazolidin-2-one products with generation of two bonds and up to two stereocenters when treated with aryl bromides and catalytic amounts of Pd-2(dba)(3)/Xantphos in the presence of (NaOBu)-Bu-t.
引用
收藏
页码:2531 / 2534
页数:4
相关论文
共 25 条
[1]   Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes [J].
Bar, GLJ ;
Lloyd-Jones, GC ;
Booker-Milburn, KI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7308-7309
[2]   Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides [J].
Bertrand, MB ;
Wolfe, JP .
TETRAHEDRON, 2005, 61 (26) :6447-6459
[3]   TETRAHYDROPYRIDONES VIA INTRAMOLECULAR UREIDOMERCURATION [J].
DANISHEFSKY, S ;
TANIYAMA, E ;
WEBB, RR .
TETRAHEDRON LETTERS, 1983, 24 (01) :11-14
[4]  
De Lucca George V., 1998, Drugs of the Future, V23, P987, DOI 10.1358/dof.1998.023.09.473829
[5]  
Dumas J, 2002, CURR OPIN DRUG DISC, V5, P718
[6]   MECHANISMS OF 1,1-REDUCTIVE ELIMINATION FROM PALLADIUM [J].
GILLIE, A ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (15) :4933-4941
[7]   Palladium(II)-catalyzed intramolecular aminocarbonylation of endo-carbamates under Wacker-type conditions [J].
Harayama, H ;
Abe, A ;
Sakado, T ;
Kimura, M ;
Fugami, K ;
Tanaka, S ;
Tamaru, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2113-2122
[8]   Palladium-catalyzed synthesis of 2,1′-disubstituted tetrahydrofurans from γ-hydroxy internal alkenes.: Evidence for alkene insertion into a Pd-O bond and stereochemical scrambling via β-hydride elimination [J].
Hay, MB ;
Wolfe, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16468-16476
[9]   Potent inhibitors of the HIV-1 protease incorporating cyclic urea P1-P2 scaffold [J].
Kazmierski, WM ;
Furfine, E ;
Gray-Nunez, Y ;
Spaltenstein, A ;
Wright, L .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (22) :5685-5687
[10]   Synthesis of a cyclic urea as a nonnatural biopolymer scaffold [J].
Kim, JM ;
Wilson, TE ;
Norman, TC ;
Schultz, PG .
TETRAHEDRON LETTERS, 1996, 37 (30) :5309-5312