Nickel(II)-catalyzed Michael additions.: Formation of quaternary centers and diastereoselective addition of enantiopure N-acetoacetyl-4-benzyloxazolidin-2-one

被引：53

作者：

Clariana, J

Gálvez, N

Marchi, C

Mañas, MM ^{[1
]}

Vallribera, A

Molins, E

机构：

[1] Univ Autonoma Barcelona, Dept Chem, E-08193 Barcelona, Spain

[2] CSIC, Inst Ciencia Mat Barcelona, E-08193 Cerdanyola, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 23期

关键词：

nickel catalysis; conjugate addition; quaternary centers; chiral induction; amides of malonic acid;

D O I：

10.1016/S0040-4020(99)00358-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ni(acac)(2) and Ni(salicylaldehydate)(2) are effective catalysts for conjugate additions of 2-methyl-1,3-dicarbonyl compounds to Michael accepters, Significant diastereomeric excesses are obtained in the Michael additions of enantiopure N-acetoacetyl-4-benzyloxazolidinones. Reaction of the latter compound with aryl isocyanates affords unsymmetrical diamides of malonic acid, (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7331 / 7344

页数：14

相关论文

共 42 条

[21] Highly efficient ytterbium triflate catalyzed Michael additions of alpha-nitroesters in water [J].

Keller, E ;

Feringa, BL .

SYNLETT, 1997, (07) :842-&

[22] Yb(OTf)(3)-catalyzed Michael addition reactions of beta-ketoesters on silica gel supports and at high pressure [J].

Kotsuki, H ;

Arimura, K .

TETRAHEDRON LETTERS, 1997, 38 (43) :7583-7586

[23] REGIOSELECTIVITY IN ALDOL CYCLIZATION [J].

KREISER, W ;

BELOW, P .

TETRAHEDRON LETTERS, 1981, 22 (05) :429-432

[24]

Lee HK, 1996, SYNLETT, P1209

[25] DEVELOPMENT OF METHODS FOR THE SYNTHESIS OF CHIRAL, HIGHLY FUNCTIONALIZED 2-AMINO-4-ARYL-4H-PYRANS [J].

MARCO, JL ;

MARTIN, N ;

MARTINEZGRAU, A ;

SEOANE, C ;

ALBERT, A ;

CANO, FH .

TETRAHEDRON, 1994, 50 (11) :3509-3528

[26] ASYMMETRIC ALKYLATION OF BETA-KETOESTERS - SYNTHESIS AND MICHAEL ADDITIONS OF A CHIRAL SULTAM-DERIVED ACETOACETYL EQUIVALENT [J].

MARTIN, N ;

MARTINEZGRAU, A ;

SEOANE, C ;

MARCO, JL .

TETRAHEDRON LETTERS, 1993, 34 (35) :5627-5630

[27] Transformations of beta-dicarbonyl compounds by reactions of their transition metal complexes with carbon and oxygen electrophiles [J].

MorenoManas, M ;

Marquet, J ;

Vallribera, A .

TETRAHEDRON, 1996, 52 (10) :3377-3401

[28] Diastereoselective alkylation of 8-phenylmenthyl 2-methylacetoacetate. Preparation of enantiomerically pure 4,4-disubstituted 2-pyrazolin-5-ones [J].

MorenoManas, M ;

Sebastian, RM ;

Vallribera, A ;

Molins, E ;

Espinosa, E .

TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1525-1527

[29] DIASTEREOSELECTIVE ALKYLATION OF CHIRAL DERIVATIVES OF ACETOACETIC ACID [J].

MORENOMANAS, M ;

SEBASTIAN, RM ;

VALLRIBERA, A ;

MOLINS, E .

TETRAHEDRON, 1995, 51 (39) :10795-10800

[30] Ruthenium-catalyzed aldol and Michael reactions of nitriles. Carbon-carbon bond formation by alpha-C-H activation of nitriles [J].

Murahashi, SI ;

Naota, T ;

Taki, H ;

Mizuno, M ;

Takaya, H ;

Komiya, S ;

Mizuho, Y ;

Oyasato, N ;

Hiraoka, M ;

Hirano, M ;

Fukuoka, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (50) :12436-12451

← 1 2 3 4 5 →