LANTHANIDE(III) TRIFLUOROMETHANESULFONATES AS EXTRAORDINARILY EFFECTIVE NEW CATALYSTS FOR THE AMINOLYSIS OF 1,2-EPOXIDES

被引：203

作者：

CHINI, M ^{[1
]}

CROTTI, P ^{[1
]}

FAVERO, L ^{[1
]}

MACCHIA, F ^{[1
]}

PINESCHI, M ^{[1
]}

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,I-56126 PISA,ITALY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 03期

关键词：

D O I：

10.1016/0040-4039(94)85073-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lanthanide(lll) trifluoromethanesulfonates (triflates), such as Yb(OTf)3, Nd(OTf)3 and Gd(OTf)3, catalyze in a extraordinarily efficient way the aminolysis of 1,2-epoxides, affording the corresponding beta-amino alcohols, at room temperature and in a non-protic solvent (CH2Cl2 or toluene), in very good yields. The reactions are completely anti stereoselective and highly regioselective.

引用

页码：433 / 436

页数：4

共 6 条

[1] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .3. AMINOLYSIS AND AZIDOLYSIS 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, 1991, 56 (25) :7043-7048

[2] REGIOALTERNATING SELECTIVITY IN THE METAL SALT CATALYZED AMINOLYSIS OF STYRENE OXIDE [J].

CHINI, M ;

CROTTI, P ;

MACCHIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5939-5942

[3] METAL-SALTS AS NEW CATALYSTS FOR MILD AND EFFICIENT AMINOLYSIS OF OXIRANES [J].

CHINI, M ;

CROTTI, P ;

MACCHIA, F .

TETRAHEDRON LETTERS, 1990, 31 (32) :4661-4664

[4] USE OF LANTHANIDE(III) IONS AS CATALYSTS FOR THE REACTIONS OF AMINES WITH NITRILES [J].

FORSBERG, JH ;

SPAZIANO, VT ;

BALASUBRAMANIAN, TM ;

LIU, GK ;

KINSLEY, SA ;

DUCKWORTH, CA ;

POTERUCA, JJ ;

BROWN, PS ;

MILLER, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1017-1021

[5] REACTION OF CYANOTRIMETHYLSILANE WITH OXIRANES UNDER YB(CN)3 CATALYSIS [J].

MATSUBARA, S ;

ONISHI, H ;

UTIMOTO, K .

TETRAHEDRON LETTERS, 1990, 31 (43) :6209-6212

[6] OXIRANE RING-OPENING REACTIONS WITH THIOLS CATALYZED BY LANTHANIDE COMPLEXES [J].

VOUGIOUKAS, AE ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1987, 28 (48) :6065-6068

← 1 →