Successive copper(I)-catalyzed cross-couplings in one pot: A novel and efficient starting point for synthesis of carbapenems

被引：53

作者：

Jiang, Biao ^{[1
]}

Tian, Hua ^{[1
]}

Huang, Zuo-Gang ^{[1
]}

Xu, Min ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 13期

关键词：

D O I：

10.1021/ol800845r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient approach for synthesizing a series of 2-sulfide carbapenems has been developed using two successive Cu(I)-catalyzed cross-couplings in a single pot. The method involves highly selective intramolecular coupling of lactam and dihaloalkene using 2,2'-bipyridine as a ligand, followed by intermolecular C-S formation in the presence of another ligand (1,10-phenanthroline, PPh3) and mercaptan.

引用

页码：2737 / 2740

页数：4

共 45 条

[31] CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates [J].

Pan, XH ;

Cai, Q ;

Ma, DW .

ORGANIC LETTERS, 2004, 6 (11) :1809-1812

[32]

Pyun DK, 2001, SYNLETT, P1950

[33] NOVEL SYNTHESIS OF THE CARBAPEN-2-EM RING-SYSTEM [J].

RATCLIFFE, RW ;

SALZMANN, TN ;

CHRISTENSEN, BG .

TETRAHEDRON LETTERS, 1980, 21 (01) :31-34

[34] A STEREOCONTROLLED SYNTHESIS OF (+)-THIENAMYCIN [J].

SALZMANN, TN ;

RATCLIFFE, RW ;

CHRISTENSEN, BG ;

BOUFFARD, FA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (19) :6161-6163

[35] Practical synthesis of (R)-4-mercaptopyrrolidine-2-thione from L-aspartic acid.: Preparation of a novel orally active 1-β-methylcarbapenem, TA-949 [J].

Seki, M ;

Yamanaka, T ;

Kondo, K .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) :517-522

[36] Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution [J].

Shen, RC ;

Porco, JA .

ORGANIC LETTERS, 2000, 2 (09) :1333-1336

[37] Construction of β-haloenamides via direct copper-promoted coupling of lactams with 2-chloro and 2-bromo vinyliodides [J].

Sun, CX ;

Camp, JE ;

Weinreb, SM .

ORGANIC LETTERS, 2006, 8 (09) :1779-1781

[38]

SUNAGAWA M, 1994, CHEM PHARM BULL, V42, P1381

[39]

Sunagawa M, 2001, HETEROCYCLES, V54, P497

[40] THREO SELECTIVE CROSS ALDOL CONDENSATION WITH THIOAMIDE ENOLATES GENERATED BY A MICHAEL ADDITION OF ORGANOMETALLICS TO UNSATURATED THIOAMIDES [J].

TAMARU, Y ;

HIOKI, T ;

YOSHIDA, Z .

TETRAHEDRON LETTERS, 1984, 25 (50) :5793-5796

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