Enantioselective Pummerer-type rearrangement by reaction of O-silylated ketene acetal with enantiopure alpha-substituted sulfoxides

被引：7

作者：

Kita, Y ^{[1
]}

Shibata, N ^{[1
]}

Fukui, S ^{[1
]}

Bando, M ^{[1
]}

Fujita, S ^{[1
]}

机构：

[1] OTSUKA PHARMACEUT CO LTD,TOKUSHIMA INST NEW DRUG RES 2,TOKUSHIMA 77101,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 12期

关键词：

D O I：

10.1039/a702020a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral non-racemic alpha-substituted sulfoxides have-been allowed to-react with O-silylated ketene acetals: in the presence of a catalytic amount of ZnI2 in THF to give chiral non-racemic alpha-siloxy sulfides in >99% ee. This is the highest enantioselectivity reported to date for the Pummerer reaction.

引用

页码：1763 / 1767

页数：5

共 33 条

[1] ENANTIOSELECTIVE TRANSFORMATIONS AND RACEMIZATION STUDIES OF HETEROATOM SUBSTITUTED ORGANOLITHIUM COMPOUNDS [J].

AGGARWAL, VK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (02) :175-177

[2] THE STRUCTURE OF LITHIUM COMPOUNDS OF SULFONES, SULFOXIMIDES, SULFOXIDES, THIOETHERS AND 1,3-DITHIANES, NITRILES, NITRO-COMPOUNDS AND HYDRAZONES [J].

BOCHE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (03) :277-297

[3]

DURST T, 1969, ADVANCES ORGANIC CHE, V6, P285

[4] STUDIES ON THE STEREOSELECTIVE METHYLATION OF ALPHA-SULFINYL CARBANIONS GENERATED FROM 3 ISOMERIC PYRIDYLMETHYL PARA-TOLYL SULFOXIDES AND BENZYL 2-PYRIDYL SULFOXIDE [J].

FURUKAWA, N ;

HOSONO, E ;

FUJIHARA, H ;

OGAWA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (02) :461-465

[5] 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-&

[6] CHIRAL LITHIUM-1-OXYALKANIDES BY ASYMMETRIC DEPROTONATION - ENANTIOSELECTIVE SYNTHESIS OF 2-HYDROXYALKANOIC ACIDS AND SECONDARY ALKANOLS [J].

HOPPE, D ;

HINTZE, F ;

TEBBEN, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12) :1422-1424

[7]

HORNER L, 1959, LIEBIGS ANN CHEM, V626, P19

[8]

HORNER L, 1960, LIEBIGS ANN CHEM, V631, P198

[9] 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

[10] 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

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