ASYMMETRIC INDUCTION IN [2+2]CYCLOADDITION OF CHLOROSULFONYL ISOCYANATE TO 1,2-O-ISOPROPYLIDENE-3-O-VINYL-GLYCOFURANOSES

被引：39

作者：

KALUZA, Z ^{[1
]}

FURMAN, B ^{[1
]}

PATEL, M ^{[1
]}

CHMIELEWSKI, M ^{[1
]}

机构：

[1] STEVENS INST TECHNOL,HOBOKEN,NJ 07030

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)86293-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinylglycofuranoses is presented. Bulky substituent at the C-4 carbon atom promotes excellent stereoselectivity affording (R) configuration at the C-4' carbon atom of the azetidinone ring. Intramolecular cyclization in compounds 9 or 12 provides diastereomeric cephem 20 and 21.

引用

收藏

页码：2179 / 2186

页数：8

相关论文

共 22 条

[1]

ARNOLD T, 1989, J CHEM SOC P1, P1169

[2]

BERNARDO SD, 1985, J ORG CHEM, V50, P3457

[3] ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY ESTERS BY REFORMATSKY REACTIONS AND AMIDE BASE MEDIATED CONDENSATIONS [J].

BRANDANGE, S ;

JOSEPHSON, S ;

MORCH, L ;

VALLEN, S .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1981, 35 (04) :273-277

[4]

DUHAMEL L, 1991, SYNLETT, P807

[5] ENANTIOSELECTIVE METHYLATION OF GLYCINE INFLUENCE OF THE STRUCTURE OF THE CHIRAL NUCLEOFUGAL [J].

DUHAMEL, P ;

EDDINE, JJ ;

VALNOT, JY .

TETRAHEDRON LETTERS, 1987, 28 (33) :3801-3804

[6] ENANTIOSELECTIVE SYNTHESES WITH TITANIUM-CARBOHYDRATE COMPLEXES .5. ENANTIOSELECTIVE AND DIASTEREOSELECTIVE ALDOL-REACTION OF 2,6-DIMETHYLPHENYL PROPIONATE USING TITANIUM-CARBOHYDRATE COMPLEXES [J].

DUTHALER, RO ;

HEROLD, P ;

WYLERHELFER, S ;

RIEDIKER, M .

HELVETICA CHIMICA ACTA, 1990, 73 (03) :659-673

[7] ASYMMETRIC REDUCTION OF KETONES WITH SODIUM-BOROHYDRIDE IN THE PRESENCE OF HYDROXYMONOSACCHARIDE DERIVATIVES [J].

HIRAO, A ;

MOCHIZUKI, H ;

NAKAHAMA, S ;

YAMAZAKI, N .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1720-1722

[8] ASYMMETRIC REDUCTION OF AROMATIC KETONES WITH REAGENTS PREPARED FROM SODIUM-BOROHYDRIDE AND VARIOUS CARBOXYLIC-ACIDS IN THE PRESENCE OF 1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE [J].

HIRAO, A ;

ITSUNO, S ;

OWA, M ;

NAGAMI, S ;

MOCHIZUKI, H ;

ZOOROV, HHA ;

NIAKAHAMA, S ;

YAMAZAKI, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (03) :900-905

[9] ASYMMETRIC REDUCTION OF PROCHIRAL AROMATIC KETONES WITH MODIFIED REAGENTS PREPARED FROM SODIUM-BOROHYDRIDE AND CARBOXYLIC-ACIDS IN THE PRESENCE OF 1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE [J].

HIRAO, A ;

NAKAHAMA, S ;

MOCHIZUKI, H ;

ITSUNO, S ;

YAMAZAKI, N .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) :4231-4233

[10] ASYMMETRIC REDUCTION OF AROMATIC KETONES WITH REAGENTS PREPARED FROM NABH4 AND ZNCL2 IN THE PRESENCE OF 1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE [J].

HIRAO, A ;

OHWA, M ;

ITSUNO, S ;

MOCHIZUKI, H ;

NAKAHARA, S ;

YAMAZAKI, N .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (05) :1424-1428