NOVEL, METAL-CATALYZED CARBONYLATION OF ACYCLIC ORGANIC-COMPOUNDS - THE REGIOSPECIFIC CARBONYLATION OF N,S-ACETALS

被引：31

作者：

KHUMTAVEEPORN, K ^{[1
]}

ALPER, H ^{[1
]}

机构：

[1] UNIV OTTAWA,DEPT CHEM,10 MARIE CURIE ST,OTTAWA K1N 6N5,ONTARIO,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 06期

关键词：

D O I：

10.1021/jo00085a034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rhodium(I) complex, [Rh(CO)2Cl]2, catalyzes the regiospecific carbonylation of N,S-acetals of structural type PhCH2SCH2NR1R2 to form PhCH2COSCH2NR1R2 in 68-92% isolated yields. Exclusive insertion of carbon monoxide occurs into the other sulfur-carbon bond of RSCH(Ph)-NR3R4 (R = PhCH2, n-C11H23) affording RSCOCH(Ph)NR3R4 in 46-83% yield.

引用

页码：1414 / 1417

页数：4

共 12 条

[1] A NOVEL SYNTHESIS OF BETA-LACTAMS [J].

ALPER, H ;

PERERA, CP ;

AHMED, FR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (05) :1289-1291

[2]

BARRETT GC, 1979, COMPREHENSIVE ORGANI, V3, P55

[3] ENANTIOSPECIFIC AND STEREOSPECIFIC RHODIUM(I)-CATALYZED CARBONYLATION AND RING EXPANSION OF AZIRIDINES - ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS AND THE KINETIC RESOLUTION OF AZIRIDINES [J].

CALET, S ;

URSO, F ;

ALPER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :931-934

[4]

Colquhoun H.M., 1991, CARBONYLATION, P191

[5]

Giordano G., 1979, INORG SYNTH, V19, P218

[6]

KHUMTAVEEPORN K, UNPUB

[7]

MURAHASHI S, 1988, J CHEM SOC CHEM COMM, V24, P1578

[8] REACTION OF GRIGNARD REAGENTS WITH N,N-DIALKYL-N-(PHENYLTHIOMETHYL)AMINES [J].

POLLAK, IE ;

TRIFUNAC, AD ;

GRILLOT, GF .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) :272-&

[9] NOVEL SYNTHESIS OF PYRROLIDINONES BY COBALT CARBONYL CATALYZED CARBONYLATION OF AZETIDINES - A NEW RING-EXPANSION CARBONYLATION REACTION OF 2-VINYLAZETIDINES TO TETRAHYDROAZEPINONES [J].

ROBERTO, D ;

ALPER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7539-7543

[10]

SPEARS GW, 1991, SYNLETT, P91

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