REGIOCONTROL IN NUCLEOPHILIC RING-OPENING OF CHIRAL EPOXIDES OF CHEMOENZYMATIC ORIGIN

被引:13
作者
GUANTI, G [1 ]
MERLO, V [1 ]
NARISANO, E [1 ]
机构
[1] CNR,CTR STUDIO CHIM COMPOSTI CICLOALIFATICI & AROMATI,I-16132 GENOA,ITALY
关键词
D O I
10.1016/S0040-4020(01)89574-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Homochiral cis epoxides derived from enzymatically asymmetrized tris(hydroxymethyl)methane equivalents (THYM*) are regioselectively opened by carbon based-nucleophiles (alkyl groups or cyanides) and halides in the presence of Lewis acids. Enantio- and diastereodivergent synthesis of branched triols is reported.
引用
收藏
页码:12245 / 12258
页数:14
相关论文
共 45 条
[1]   BORON FLUORIDE PROMOTED OPENING OF EPOXIDES BY ORGANOCOPPER AND CUPRATE REAGENTS [J].
ALEXAKIS, A ;
JACHIET, D ;
NORMANT, JF .
TETRAHEDRON, 1986, 42 (20) :5607-5619
[2]   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
[3]   REGIOSELECTIVITY AND STEREOSELECTIVITY OF 3-MEMBERED RING-OPENING OF SOME 3,4-EPOXYTETRAHYDROPYRANS AND OF CORRESPONDING EPIBROMONIUM IONS [J].
BERTI, G ;
CATELANI, G ;
FERRETTI, M ;
MONTI, L .
TETRAHEDRON, 1974, 30 (22) :4013-4020
[4]   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
[5]   REGIO AND DIASTEREOSELECTIVE OXYGEN ASSISTED OPENING BY MONO-CHLOROBORANE-DIMETHYLSULFIDE OF EPOXIDES TO ANTICHLOROHYDRINS [J].
BOVICELLI, P ;
LUPATTELLI, P ;
BERSANI, MT ;
MINCIONE, E .
TETRAHEDRON LETTERS, 1992, 33 (41) :6181-6182
[6]  
CARDANI S, 1986, SYNTHESIS-STUTTGART, P1032
[7]   TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].
CARON, M ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560
[8]  
CHINI M, 1994, TETRAHEDRON, V50, P1261
[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]   REGIOSELECTIVE OPENING OF 2,3-EPOXY ALCOHOLS WITH ORGANOCUPRATES - ENHANCED C-2 SELECTIVITY THROUGH SOLVENT EFFECTS [J].
CHONG, JM ;
CYR, DR ;
MAR, EK .
TETRAHEDRON LETTERS, 1987, 28 (42) :5009-5012