Diastereoselective cycloadditions of nitrilimines to enantiopure acrylamides

被引：14

作者：

Garanti, L

Molteni, G

Pilati, T

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] CNR, Ist Sci & Tecnol Mol, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(02)00258-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The diastereoselective cycloaddition of the nitrilimine 2 with enantiopure acrylamides 3 was exploited to obtain enantiopure 4,5-dihydropyrazoles 4 and 5. Basic hydrolysis of the cycloadducts gave the dicarboxy derivatives 6 and 7 or 8 and 9, which are of potential interest as new chiral building blocks. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1285 / 1289

页数：5

相关论文

共 24 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2]

BARALDI PG, 1987, SYNTHESIS-STUTTGART, P857

[3]

CINQUINI M, 1995, STEREOSELECTIVE SY C, V21, P2953

[4] An improved synthesis of enantiomerically pure CIP-AS, potent and selective AMPA-kainate receptor agonist [J].

Conti, P ;

Roda, G ;

Negra, FFB .

TETRAHEDRON-ASYMMETRY, 2001, 12 (09) :1363-1367

[5] AMINO-ACIDS .14. DIASTEREOSELECTIVE ADDITION OF BENZENESULFENYL CHLORIDE TO 1-ACRYLOYLPROLINE ESTERS [J].

EFFENBERGER, F ;

ISAK, H .

CHEMISCHE BERICHTE, 1989, 122 (03) :545-551

[6]

ELABADELAH MM, 1988, HETEROCYCLES, V27, P917

[7] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256

[8] Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: Applications in organic synthesis [J].

Frederickson, M .

TETRAHEDRON, 1997, 53 (02) :403-425

[9] DELTA-4-ISOXAZOLINES (2,3-DIHYDROISOXAZOLES) [J].

FREEMAN, JP .

CHEMICAL REVIEWS, 1983, 83 (03) :241-261

[10] Metal-catalyzed asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

ACTA CHEMICA SCANDINAVICA, 1996, 50 (08) :652-660