A SIMPLE ROUTE TO SYN ALPHA-AMINO-BETA-HYDROXY ESTERS BY C-2 REGIOSELECTIVE OPENING OF ALPHA,BETA-EPOXY ESTERS WITH METAL-HALIDES

被引：35

作者：

RIGHI, G ^{[1
]}

RUMBOLDT, G ^{[1
]}

BONINI, C ^{[1
]}

机构：

[1] UNIV BASILICATA,DIPARTIMENTO CHIM,I-85100 POTENZA,ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 48期

关键词：

D O I：

10.1016/0040-4020(95)00873-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha,beta-Epoxy esters are opened by NaX (X = I, Br) in a regio and stereoselective fashion to beta-hydroxy-alpha-halo esters, which represent suitable precursors of syn alpha-amino-beta-hydroxy esters and beta-hydroxy esters.

引用

页码：13401 / 13408

页数：8

共 21 条

[1] SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2 [J].

BEHRENS, CH ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5696-5704

[2] C-1 REACTIVITY OF 2,3-EPOXY ALCOHOLS VIA OXIRANE OPENING WITH METAL-HALIDES - APPLICATIONS AND SYNTHESIS OF NATURALLY-OCCURRING 2,3-OCTANEDIOL, MURICATACIN, 3-OCTANOL, AND 4-DODECANOLIDE [J].

BONINI, C ;

FEDERICI, C ;

ROSSI, L ;

RIGHI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4803-4812

[3] AN EASY PROCEDURE FOR THE HIGHLY REGIOSELECTIVE CONVERSION OF EPOXIDES TO HALOHYDRINS [J].

BONINI, C ;

GIULIANO, C ;

RIGHI, G ;

ROSSI, L .

SYNTHETIC COMMUNICATIONS, 1992, 22 (13) :1863-1870

[4] REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES [J].

BONINI, C ;

RIGHI, G .

SYNTHESIS-STUTTGART, 1994, (03) :225-238

[5] ENANTIOSELECTIVE AND STEREOSELECTIVE ROUTE TO THE TAXOL SIDE-CHAIN VIA ASYMMETRIC EPOXIDATION OF TRANS-CINNAMYL ALCOHOL AND SUBSEQUENT EPOXIDE RING-OPENING [J].

BONINI, C ;

RIGHI, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (24) :2767-2768

[6] DIOLS OBTAINED VIA CHEMOSELECTIVE AND REGIOSELECTIVE RING-OPENING OF EPOXY ALCOHOLS - A STRAIGHTFORWARD SYNTHESIS OF 2S,3S-OCTANEDIOL [J].

BONINI, C ;

RIGHI, G .

TETRAHEDRON, 1992, 48 (08) :1531-1538

[7]

BONINI C, 1994, TETRAHEDRON LETT, V35, P797

[8]

BORDWELL FG, 1964, J AM CHEM SOC, V64, P4645

[9]

CALDWELL CG, 1990, SYNTHESIS-STUTTGART, P34

[10] REGIOSELECTIVE OPENINGS OF 2,3-EPOXY ACIDS WITH ORGANOCUPRATES [J].

CHONG, JM ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1985, 26 (39) :4683-4686

← 1 2 3 →