A versatile method for the synthesis of 3-alkoxycarbonyl β-lactam derivatives

被引：61

作者：

Jiao, L ^{[1
]}

Zhang, QF ^{[1
]}

Liang, Y ^{[1
]}

Zhang, SW ^{[1
]}

Xu, JX ^{[1
]}

机构：

[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 02期

关键词：

D O I：

10.1021/jo052135z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Ketene-imine cvcloaddition reactions (the Staudinger reaction) of ethoxycarbonyl(phenylthio)ketene with various imines and subsequent desulfurization reactions were employed to synthesize 3-ethoxycarbonyl beta-lactam derivatives. The results indicate that the current approach provides a convenient, mild, and versatile method for synthesizing a variety of 3-alkoxycarbonyl trans-beta-lactam derivatives with good to excellent yields and diastereoselectivies.

引用

收藏

页码：815 / 818

页数：4

相关论文

共 45 条

[1] Enantioselective intramolecular C-H insertion route to a key intermediate for the synthesis of trinem antibiotics [J].

Anada, M ;

Hashimoto, S .

TETRAHEDRON LETTERS, 1998, 39 (49) :9063-9066

[2] Highly enantioselective construction of the key azetidin-2-ones for the synthesis of carbapenem antibiotics via intramolecular C-H insertion reactions of α-methoxycarbonyl-α-diazoacetamides catalysed by chiral dirhodium(II) carboxylates [J].

Anada, M ;

Watanabe, N ;

Hashimoto, S .

CHEMICAL COMMUNICATIONS, 1998, (15) :1517-1518

[3] Mn(III)-promoted sulfur-directed 4-exo-trig radical cyclization of enamides to β-lactams [J].

Attenni, B ;

Cerreti, A ;

D'Annibale, A ;

Resta, S ;

Trogolo, C .

TETRAHEDRON, 1998, 54 (39) :12029-12038

[4] A facile Lewis acid-promoted allylation of azetidin-2-ones [J].

Bari, SS ;

Venugopalan, P ;

Arora, R .

TETRAHEDRON LETTERS, 2003, 44 (05) :895-897

[5] A carbene insertion route to β-lactam fused cyclic enediynes [J].

Basak, A ;

Mandal, S .

TETRAHEDRON LETTERS, 2002, 43 (23) :4241-4243

[6] PPL-catalysed hydrolysis of 3,4-disubstituted β-lactams:: Effect of chain length and stereochemistry on the enantioselectivity [J].

Basak, A ;

Bhattacharya, G ;

Bdour, HMM .

TETRAHEDRON, 1998, 54 (23) :6529-6538

[7] Differential effects of stereochemistry and C-4 substituents on the enantioselectivity of PLE and PPL catalysed hydrolysis of 3,4-disubstituted beta-lactams [J].

Basak, A ;

Mahato, T ;

Bhattacharya, G ;

Mukherjee, B .

TETRAHEDRON LETTERS, 1997, 38 (04) :643-646

[8] SULFENYLATION AND HALOGENATION REACTIONS LEADING SELECTIVELY TO CIS-CARBAPENEM PRECURSORS - STEREOSPECIFIC SYNTHESIS OF (+/-)-6-EPITHIENAMYCIN [J].

BATESON, JH ;

QUINN, AM ;

SOUTHGATE, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (15) :1151-1152

[9] STUDIES ON BETA-LACTAMS .36. MONOCYCLIC CIS-BETA-LACTAMS VIA PENAMS AND CEPHAMS [J].

BOSE, AK ;

MANHAS, MS ;

CHIB, JS ;

CHAWLA, HPS ;

DAYAL, B .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (19) :2877-2884

[10] LIGAND EFFECTS IN THE RHODIUM(II)-CATALYZED REACTIONS OF ALPHA-DIAZOAMIDES - OXINDOLE FORMATION IS PROMOTED BY THE USE OF RHODIUM(II) PERFLUOROCARBOXAMIDE CATALYSTS [J].

BROWN, DS ;

ELLIOTT, MC ;

MOODY, CJ ;

MOWLEM, TJ ;

MARINO, JP ;

PADWA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2447-2455

← 1 2 3 4 5 →