REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES

被引:288
作者
BONINI, C [1 ]
RIGHI, G [1 ]
机构
[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO CHIM,CNR,CTR STUDIO CHIM SOSTANZE ORGAN NAT,I-00185 ROME,ITALY
来源
SYNTHESIS-STUTTGART | 1994年 / 03期
关键词
D O I
10.1055/s-1994-25445
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Recent developments in the regio-, chemo- and stereoselective oxirane cleavage by new halogenating reagents allow obtention of various vicinal halohydrins. Also, epoxy alcohols and other functionalized oxiranes can be conveniently converted into the corresponding halohydrins. Some of the new methodologies have been successfully applied to the preparation of optically active fragments toward the synthesis to more complex molecules and natural products.
引用
收藏
页码:225 / 238
页数:14
相关论文
共 99 条
[1]   MILD AND STEREOCONTROLLED SYNTHESIS OF IODOHYDRINS AND BROMOHYDRINS BY X2-TI(O-ISO-PR)4 OPENING OF EPOXY ALCOHOLS [J].
ALVAREZ, E ;
NUNEZ, MT ;
MARTIN, VS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3429-3431
[2]  
ARANDA G, 1965, B SOC CHIM FR, P1890
[3]  
ARANDA G, 1966, B SOC CHIM FR, P2850
[4]   NEW SYNTHETIC ROUTES TO BETA-FLUORO BETA-PHENYLLACTIC ACID-DERIVATIVES AND BETA-FLUOROCYANOHYDRINS [J].
AYI, AI ;
REMLI, M ;
CONDOM, R ;
GUEDJ, R .
JOURNAL OF FLUORINE CHEMISTRY, 1981, 17 (06) :565-580
[5]   A HIGHLY REGIOSELECTIVE CONVERSION OF EPOXIDES TO HALOHYDRINS BY LITHIUM HALIDES [J].
BAJWA, JS ;
ANDERSON, RC .
TETRAHEDRON LETTERS, 1991, 32 (26) :3021-3024
[6]  
BARROW KD, 1983, MARINE NATURAL PRODU, V5, P51
[7]  
Bartlett P. A., 1984, ASYMMETRIC SYNTHESIS, V3, P411
[8]   CONVERSION OF EPOXIDES TO BROMOHYDRINS BY B-BROMOBIS (DIMETHYLAMINO) BORANE [J].
BELL, TW ;
CIACCIO, JA .
TETRAHEDRON LETTERS, 1986, 27 (07) :827-830
[9]   CLEAVAGE OF ETHERS [J].
BHATT, MV ;
KULKARNI, SU .
SYNTHESIS-STUTTGART, 1983, (04) :249-282
[10]  
Boguslavskaya LS, 1972, RUSS CHEM REV, V41, P740