Domino palladium(II)-mediated rearrangement-oxidative cyclization of β-aminocyclopropanols

被引:24
作者
Cicchi, S
Revuelta, J
Zanobini, A
Betti, M
Brandi, A
机构
[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50019 Sesto Fiorentino, FI, Italy
[2] CNR, ICCOM, I-50019 Sesto Fiorentino, FI, Italy
关键词
domino reactions; palladium; Wacker reactions; heterocycles; catalysis;
D O I
10.1055/s-2003-42122
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Aminocyclopropanols were transformed, in a domino process catalyzed by Pd(II) salts, into the corresponding 2,3-dihydro-1H-pyridin-4-ones. Conversely the use of a Pd(0) derivative, Pd(dba)(2), afforded the corresponding tetrahydropyrid-4-ones. The saturated derivatives were also obtained, in better yields, using Pd(II) and Cu(OAc)(2) as stoichiometric oxidant.
引用
收藏
页码:2305 / 2308
页数:4
相关论文
共 35 条
[1]   Thermal rearrangements of vinylcyclopropanes to cyclopentenes [J].
Baldwin, JE .
CHEMICAL REVIEWS, 2003, 103 (04) :1197-1212
[2]   Heterocycles from alkylidenecyclopropanes [J].
Brandi, A ;
Cicchi, S ;
Cordero, FM ;
Goti, A .
CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269
[3]  
BRANDI A, 1993, SYNLETT, P1
[4]   REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .2. SYNTHESIS AND REARRANGEMENT OF TETRAHYDROISOXAZOLE-5-SPIROCYCLOPROPANES - PREPARATION OF PRECURSORS OF QUINOLIZINE, ISOQUINOLINE, AND INDOLE ALKALOIDS [J].
BRANDI, A ;
GARRO, S ;
GUARNA, A ;
GOTI, A ;
CORDERO, F ;
DESARLO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2430-2434
[5]   CATALYTIC HYDROGENOLYSIS OF METHYL 2-SILOXYCYCLOPROPANECARBOXYLATES - INVESTIGATIONS REGARDING CHEMOSELECTIVITY, REGIOSELECTIVITY, AND STEREOSELECTIVITY [J].
BRUCKNER, C ;
REISSIG, HU .
CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (04) :617-626
[6]   Indium-mediated reduction of hydroxylamines to amines [J].
Cicchi, S ;
Bonanni, M ;
Cardona, F ;
Revuelta, J ;
Goti, A .
ORGANIC LETTERS, 2003, 5 (10) :1773-1776
[7]   1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL [J].
CICCHI, S ;
GOTI, A ;
BRANDI, A ;
GUARNA, A ;
DESARLO, F .
TETRAHEDRON LETTERS, 1990, 31 (23) :3351-3354
[8]  
DEMEIJERE A, 1997, HOUBENWEYL METHODS E, V1
[9]   The Kulinkovich reaction on lactones. A convenient approach to functionalized cyclopropanols [J].
Esposito, A ;
Taddei, M .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9245-9248
[10]   Derailing the Wacker oxidation: Development of a palladium-catalyzed amidation reaction [J].
Gaunt, MJ ;
Spencer, JB .
ORGANIC LETTERS, 2001, 3 (01) :25-28