ITERATIVE SYN-1,3,5-TRIOL SYNTHESIS UTILIZING THE REACTION OF BETA-(TRIMETHYLSILYL)ALKYL PHENYL SULFONES WITH OXIRANES

被引:12
作者
ACHMATOWICZ, B [1 ]
WICHA, J [1 ]
机构
[1] POLISH ACAD SCI,INST ORGAN CHEM,UL KASPRZAKA 44,PL-01224 WARSAW,POLAND
关键词
D O I
10.1016/S0957-4166(00)86085-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Partly protected triols 8a and 8b were synthesised from epoxide 1 using beta-trimethylsilyl sulphones 2a and 2a for the chain elongation and the Cardillo procedure for diastereoselective two-step epoxidation of homoallylic alcohols.
引用
收藏
页码:399 / 410
页数:12
相关论文
共 21 条
[1]   ENANTIOSELECTIVE SYNTHESIS OF THE METHYLENECYCLOPROPANE DERIVATIVE RELATED TO HYPOGLYCINE, FROM MALIC-ACID [J].
ACHMATOWICZ, B ;
KABAT, MM ;
KRAJEWSKI, J ;
WICHA, J .
TETRAHEDRON, 1992, 48 (46) :10201-10210
[2]   METHODOLOGY TO ESTABLISH 1,2-DIFUNCTIONALITY AND 1,3-DIFUNCTIONALITY FOR THE SYNTHESIS OF CARBOHYDRATE-DERIVATIVES [J].
AGER, DJ ;
EAST, MB .
TETRAHEDRON, 1992, 48 (14) :2803-2894
[3]   REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF EPOXY ALCOHOLS AND TRIOLS FROM ALLYLIC AND HOMOALLYLIC ALCOHOLS VIA IODO CARBONATES [J].
BONGINI, A ;
CARDILLO, G ;
ORENA, M ;
PORZI, G ;
SANDRI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4626-4633
[4]  
CHANTH, 1992, J ORG CHEM, V57, P6107
[5]   IODINE MONOBROMIDE (IBR) AT LOW-TEMPERATURE - A SUPERIOR PROTOCOL FOR DIASTEREOSELECTIVE CYCLIZATIONS OF HOMOALLYLIC CARBONATES [J].
DUAN, JJW ;
SPRENGELER, PA ;
SMITH, AB .
TETRAHEDRON LETTERS, 1992, 33 (43) :6439-6442
[6]   ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES [J].
HALCOMB, RL ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6661-6666
[7]   ASYMMETRIC INDUCTION IN REDUCTIVELY INITIATED [2,3]-WITTIG AND RETRO [1,4]-BROOK REARRANGEMENTS OF SECONDARY CARBANIONS [J].
HOFFMANN, R ;
BRUCKNER, R .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (06) :1471-1484
[8]   ENANTIOSELECTIVE SYNTHESIS OF THE METHYLENECYCLOPROPANE DERIVATIVE RELATED TO HYPOGLYCINE, STARTING FROM MALIC-ACID [J].
KABAT, MM ;
WICHA, J .
TETRAHEDRON LETTERS, 1991, 32 (04) :531-532
[9]   THE REACTION OF BETA-(TRIMETHYLSILYL)ALKYL PHENYL SULFONES WITH OXIRANES - A METHOD FOR STEREOCONTROLLED SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].
KABAT, MM ;
WICHA, J .
TETRAHEDRON LETTERS, 1991, 32 (08) :1073-1076
[10]  
KOCIENSKI PJ, 1979, TETRAHEDRON LETT, V21, P2649