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

被引：20

作者：

BONINI, C ^{[1
]}

RIGHI, G ^{[1
]}

机构：

[1] UNIV ROMA LA SAPIENZA,DIPARTMENTO CHIM,CNR,CTR STUDIO CHIM SOSTANZE NAT,I-00185 ROME,ITALY

来源：

TETRAHEDRON | 1992年 / 48卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(01)92240-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epoxy alcohols are regio and chemoselectively opened to the corresponding iodohydrins and then reduced in situ to diols; the application of the described procedure leads to a short asymmetric synthesis of a well known pheromone. Also homoallylic (E and Z) epoxy alcohols and its benzylated derivatives shows high preference for regioselective opening affording the corresponding 1,3 diol.

引用

页码：1531 / 1538

页数：8

共 25 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] A HIGHLY REGIOSELECTIVE CONVERSION OF EPOXIDES TO HALOHYDRINS BY LITHIUM HALIDES [J].

BAJWA, JS ;

ANDERSON, RC .

TETRAHEDRON LETTERS, 1991, 32 (26) :3021-3024

[3] SYNTHESIS OF THE PHEROMONE COMPONENTS OF THE GRAPE BORER XYLOTRECHUS-PYRRHODERUS BY MICROBIOLOGICAL REDUCTION OF AN ALPHA-DIKETONE [J].

BELRHLID, R ;

FAUVE, A ;

VESCHAMBRE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3221-3223

[4] REGIOSELECTIVE OPENING OF EPOXY ALCOHOLS - MILD CHEMOSELECTIVE AND STEREOSELECTIVE PREPARATION OF IODOHYDRINS AND 1,2-DIOLS [J].

BONINI, C ;

RIGHI, G ;

SOTGIU, G .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6206-6209

[5] A FACILE CHEMO AND REGIOSELECTIVE REDUCTIVE OPENING OF 1,2 EPOXIDES VIA FREE-RADICAL REACTION [J].

BONINI, C ;

DIFABIO, R .

TETRAHEDRON LETTERS, 1988, 29 (07) :819-822

[6] OXIRANE RINGS - STUDIES AND APPLICATIONS OF A NEW CHEMO AND REGIO SELECTIVE REDUCTIVE OPENING OF EPOXIDES [J].

BONINI, C ;

DIFABIO, R ;

SOTGIU, G ;

CAVAGNERO, S .

TETRAHEDRON, 1989, 45 (10) :2895-2904

[7] ONE POT CYCLIZATION OF EPOXYOLEFINS TO SUBSTITUTED CYCLOALKANOLS VIA FREE-RADICALS [J].

BONINI, C ;

DIFABIO, R ;

MECOZZI, S ;

RIGHI, G .

TETRAHEDRON LETTERS, 1990, 31 (37) :5369-5372

[8]

BOSE A K, 1973, Tetrahedron Letters, V18, P1619

[9]

CHATTOPADHYAY S, 1990, J CHEM RES-S, P235

[10] REGIOSELECTIVE TITANIUM MEDIATED REDUCTIVE OPENING OF 2,3-EPOXY ALCOHOLS [J].

DAI, LX ;

LOU, BL ;

ZHANG, YZ ;

GUO, GZ .

TETRAHEDRON LETTERS, 1986, 27 (36) :4343-4346

← 1 2 3 →