STEREOSELECTIVE REACTIONS OF ALME3 WITH CHIRAL ACYCLIC BETA-KETOSULFOXIDES

被引：14

作者：

CARRENO, MC ^{[1
]}

RUANO, JLG ^{[1
]}

MAESTRO, MC ^{[1
]}

GONZALEZ, MP ^{[1
]}

BUENO, AB ^{[1
]}

FISCHER, J ^{[1
]}

机构：

[1] UNIV STRASBOURG 1, CRISTALLOCHIM LAB, F-67070 STRASBOURG, FRANCE

来源：

TETRAHEDRON | 1993年 / 49卷 / 47期

关键词：

D O I：

10.1016/S0040-4020(01)80254-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The results obtained in the addition reactions of AlMe3 to acyclic beta-ketosulfoxides 1-5 are described. In the presence of ZnX2 (X=Cl,Br) reactions proceed in high yield. The diastereoselectivities achieved, ranging from 70% to 90%, make these reactions useful for the asymmetric synthesis of tertiary methyl carbinols.

引用

页码：11009 / 11018

页数：10

共 19 条

[1]

BARROS D, 1992, TETRAHEDRON LETT, V33, P2733

[2] REACTIONS OF CHIRAL 2-PARA-TOLYSULFINYLCYCLOALKANONES WITH ALME3 [J].

BUENO, AB ;

CARRENO, MC ;

FISCHER, J ;

RUANO, JLG ;

PENA, B ;

PENAS, L ;

RUBIO, A .

TETRAHEDRON LETTERS, 1991, 32 (27) :3191-3194

[3]

BUENO AB, 1988, CHEM LETT, P1541

[4] SYNTHESIS AND REDUCTION OF CHIRAL SULFINYL CYCLOHEXANONES [J].

CARRENO, MC ;

RUANO, JLG ;

RUBIO, A .

TETRAHEDRON LETTERS, 1987, 28 (41) :4861-4864

[5] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].

CARRENO, MC ;

RUANO, JLG ;

MARTIN, AM ;

PEDREGAL, C ;

RODRIGUEZ, JH ;

RUBIO, A ;

SANCHEZ, J ;

SOLLADIE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128

[6] SYNTHESIS AND HYDRIDE REDUCTIONS OF CHIRAL CYCLIC BETA-IMINOSULFOXIDES [J].

CARRENO, MC ;

DOMINGUEZ, E ;

RUANO, JLG ;

PEDREGAL, C ;

RODRIGUEZ, JH .

TETRAHEDRON, 1991, 47 (48) :10035-10044

[7] EFFICIENT METAL SALT CATALYZED AZIDOLYSIS OF EPOXIDES WITH SODIUM-AZIDE IN ACETONITRILE [J].

CHINI, M ;

CROTTI, P ;

MACCHIA, F .

TETRAHEDRON LETTERS, 1990, 31 (39) :5641-5644

[8] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES - SYNTHESIS AND REACTIONS OF THE CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 4-(BENZYLOXY)CYCLOHEXENE [J].

CHINI, M ;

CROTTI, P ;

FLIPPIN, LA ;

MACCHIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4265-4272

[9] EASY DIRECT STEREOSELECTIVE AND REGIOSELECTIVE FORMATION OF BETA-HYDROXY NITRILES BY REACTION OF 1,2-EPOXIDES WITH POTASSIUM CYANIDE IN THE PRESENCE OF METAL-SALTS [J].

CHINI, M ;

CROTTI, P ;

FAVERO, L ;

MACCHIA, F .

TETRAHEDRON LETTERS, 1991, 32 (36) :4775-4778

[10]

CHINI M, 1990, TETRAHEDRON LETT, V31, P4664

← 1 2 →