A HIGHLY ASYMMETRIC PUMMERER-TYPE CYCLIZATION OF CHIRAL, NON-RACEMIC BETA-AMIDOSULFOXIDES INDUCED BY O-SILYLATED KETENE ACETALS

被引：21

作者：

KITA, Y ^{[1
]}

SHIBATA, N ^{[1
]}

KAWANO, N ^{[1
]}

TOHJO, T ^{[1
]}

FUJIMORI, C ^{[1
]}

MATSUMOTO, K ^{[1
]}

机构：

[1] TAISHO PHARMACEUT CO LTD,RES CTR,OMIYA,SAITAMA 330,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 01期

关键词：

D O I：

10.1016/0040-4039(94)02180-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first highly asymmetric Pummerer-type cyclization of chiral, non-racemic beta-amidosulfoxides leading to enantiomerically enriched beta-lactams (80-85 % ee) is described. S-and R-sulfoxides (S-2a-d and R-2a-c) were treated with O-methyl-O-tert-butyldimethylsilyl ketene acetal (I) in the presence of a catalytic amount of ZnCl2 in CH2Cl2 to predominantly give the corresponding 4R- and 4S-beta-lactams (R-4a-d and S-4a-c) in more than 80 % ee. These results show that the stereoinduction is completely influenced by the absolute configuration of the sulfoxides.

引用

页码：115 / 118

页数：4

共 36 条

[1] SYNTHESIS OF BOTH ENANTIOMERS OF OPTICALLY PURE SATURATED AND ALPHA,BETA-UNSATURATED GAMMA-SUBSTITUTED GAMMA-LACTONES FROM CHIRAL SULFOXIDES - X-RAY MOLECULAR-STRUCTURE OF (3R,4S)-4-METHYL-4-TERT-BUTYL-3-(PARA-TOLYLTHIO)BUTANOLIDE AND OF (3R,4R)-4-(CYCLOHEX-1-ENYL)-4-METHYL-3-(PARA-TOLYLTHIO)BUTANOLIDEL [J].

ALBINATI, A ;

BRAVO, P ;

GANAZZOLI, F ;

RESNATI, G ;

VIANI, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1405-1415

[2] PUMMERER REARRANGEMENT OF 1,3-OXATHIOLAN-5-ONE S-OXIDES [J].

GLUE, S ;

KAY, IT ;

KIPPS, MR .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (18) :1158-&

[3] PREDOMINANT INTRAMOLECULAR PUMMERER REACTIONS OF SUBSTITUTED BENZYL PARA-TOLYL SULFOXIDES WITH ACETIC-ANHYDRIDE [J].

ITOH, O ;

NUMATA, T ;

YOSHIMURA, T ;

OAE, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (01) :266-269

[4] ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS USING A PUMMERER REACTION [J].

KANEKO, T ;

OKAMOTO, Y ;

HATADA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (19) :1511-1512

[5] POSSIBLE BIOMIMETIC SYNTHESIS OF BETA-LACTAMS [J].

KANEKO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5490-5492

[6] CHEMISTRY OF O-SILYLATED KETENE ACETALS .1. A SYNTHESIS OF BETA-LACTAM ANTIBIOTICS [J].

KITA, Y ;

TAMURA, O ;

SHIBATA, N ;

MIKI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (10) :1862-1864

[7] THE 1ST HIGHLY ASYMMETRIC PUMMERER-TYPE REACTION IN CHIRAL ACYCLIC SULFOXIDES - CHEMISTRY OF O-SILYLATED KETENE ACETALS [J].

KITA, Y ;

SHIBATA, N ;

YOSHIDA, N .

TETRAHEDRON LETTERS, 1993, 34 (25) :4063-4066

[8] A NOVEL ASYMMETRIC PUMMERER REACTION INDUCED BY ETHOXY VINYL ESTER [J].

KITA, Y ;

SHIBATA, N ;

KAWANO, N ;

FUKUI, S ;

FUJIMORI, C .

TETRAHEDRON LETTERS, 1994, 35 (21) :3575-3576

[9]

KITA Y, 1987, CHEM PHARM BULL, V35, P562

[10] MECHANISTIC STUDIES OF PUMMERER REACTION IN ACYCLIC SULFOXIDES INDUCED BY O-SILYLATED KETENE ACETALS [J].

KITA, Y ;

SHIBATA, N ;

YOSHIDA, N ;

FUKUI, S ;

FUJIMORI, C .

TETRAHEDRON LETTERS, 1994, 35 (16) :2569-2572

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