MECHANISTIC STUDIES OF PUMMERER REACTION IN ACYCLIC SULFOXIDES INDUCED BY O-SILYLATED KETENE ACETALS

被引：20

作者：

KITA, Y

SHIBATA, N

YOSHIDA, N

FUKUI, S

FUJIMORI, C

机构：

[1] Faculty of Pharmaceutical Sciences, Osaka University 1-6, Suita, Osaka, 565, Yamada-oka

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(00)77173-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pummerer reaction of acyclic sulfoxides with O-silylated ketene acetal has been shown to proceed with high diastereoselective deprotonation of the alpha-methylene proton. A plausible reaction mechanism involving the anti elimination process is proposed from deuterium-labeling experiment.

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页码：2569 / 2572

页数：4

相关论文

共 24 条

[1] 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-&

[2] 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

[3] 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

[4] 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

[5]

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

[6]

KITA Y, 1985, CHEM PHARM BULL, V33, P4235

[7] THE CHEMISTRY OF O-SILYLATED KETENE ACETAL - PUMMERER REARRANGEMENT OF SULFOXIDES INTO ALPHA-SILOXYSULFIDES [J].

KITA, Y ;

YASUDA, H ;

TAMURA, O ;

ITOH, F ;

TAMURA, Y .

TETRAHEDRON LETTERS, 1984, 25 (41) :4681-4682

[8]

LUCCHI OD, 1990, ORG REACTIONS, V40, P157

[9] SOME 4-THIO-DL-TETROFURANOSE DERIVATIVES AND OTHER OXIDATION PRODUCTS OF THIOLANE-3,4-DIOLS [J].

MCCORMICK, JE ;

MCELHINN.RS .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (04) :171-+

[10] ORGANOSULFUR COMPOUNDS .16. ALPHA-PHOSPHORYL SULFOXIDES .4. PUMMERER REARRANGEMENTS OF ALPHA-PHOSPHORYL SULFOXIDES AND ASYMMETRIC INDUCTION IN TRANSFER OF CHIRALITY FROM SULFUR TO CARBON [J].

MIKOLAJCZYK, M ;

ZATORSKI, A ;

GRZEJSZCZAK, S ;

COSTISELLA, B ;

MIDURA, W .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2518-2521