Syntheses of optically active 2-substituted cyclopropanecarboxylic acids from chiral α-hydroxysilane derivatives

被引:30
作者
Sakaguchi, K [1 ]
Mano, H [1 ]
Ohfune, Y [1 ]
机构
[1] Osaka City Univ, Dept Mat Sci, Grad Sch Sci, Sumiyoshi Ku, Osaka 5588585, Japan
关键词
masked chirality; alpha-hydroxysilane; optically active cyclopropanecarboxylic acid; diastereoselective cyclopropanation;
D O I
10.1016/S0040-4039(98)00759-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically active 2-alkylcyclopropanecarboxylic acids were efficiently synthesized from the chiral alpha-hydroxytrimethylsilanes via a diastereoselective cyclopropanation as the key step, (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4311 / 4312
页数:2
相关论文
共 12 条
[1]   SYNTHESIS AND ABSOLUTE CONFIGURATIONS OF SOME OPTICALLY ACTIVE CIS-AND TRANS-1,2-DISUBSTITUTED CYCLOPROPANES [J].
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (26) :7405-&
[2]   DIASTEREOSELECTIVE CYCLOPROPANATION OF CHIRAL ALLYLIC ALCOHOLS - A MORE EFFICIENT REAGENT FOR THE RELATIVE STEREOCONTROL [J].
CHARETTE, AB ;
LEBEL, H .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :2966-2967
[3]  
Dahr R. K., 1994, ALDRICHIM ACTA, V27, P43
[4]   A PRACTICAL AND EFFICIENT SYNTHESIS OF ALPHA,BETA-UNSATURATED ACYLSILANES [J].
DANHEISER, RL ;
FINK, DM ;
OKANO, K ;
TSAI, YM ;
SZCZEPANSKI, SW .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5393-5396
[5]   A CHIRAL PRIMARY ALCOHOL EQUIVALENT - SILYL-ASSISTED ASYMMETRIC INDUCTION IN THE ESTER ENOLATE CLAISEN REARRANGEMENT [J].
IRELAND, RE ;
VARNEY, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3668-3670
[6]   Epoxidation and cyclopropanation of 2-silyl-3-alkenols. A study of 1,2-asymmetric induction [J].
Landais, Y ;
ParraRapado, L .
TETRAHEDRON LETTERS, 1996, 37 (08) :1205-1208
[7]   SYNTHESIS OF (ALPHA-HYDROXYALKYL)SILANES FROM FORMYLTRIMETHYLSILANE - A NEW ROUTE TO ACETYLENIC ACYLSILANES [J].
LINDERMAN, RJ ;
SUHR, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1569-1572
[8]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096
[9]   ALLYLIC TRANSPOSITIONS OF ENANTIOMERICALLY PURE C1-ACYLOXY (E)-CROTYLSILANES - STEREOSPECIFIC SYNTHESIS OF (E)-VINYLSILANES [J].
PANEK, JS ;
SPARKS, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5564-5566
[10]  
SHIMAMOTO K, 1993, SYNLETT, P919