ALLYLSILANES IN ORGANIC-SYNTHESIS - STEREOSELECTIVE SYNTHESIS OF TRANS-ALKENE PEPTIDE ISOSTERES

被引:35
作者
DALY, MJ [1 ]
WARD, RA [1 ]
THOMPSON, DF [1 ]
PROCTER, G [1 ]
机构
[1] UNIV SALFORD,DEPT CHEM & APPL CHEM,SALFORD M5 4WT,LANCS,ENGLAND
关键词
D O I
10.1016/0040-4039(95)01528-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lactones obtained by the diastereoselective dihydroxylation of ester-allylsilanes have been used in the stereocontrolled synthesis of trans-alkene dipeptide isosteres.
引用
收藏
页码:7545 / 7548
页数:4
相关论文
共 20 条
[1]   A CONCISE ENANTIOSELECTIVE SYNTHESIS OF TRANS-OLEFIN DIPEPTIDE ISOSTERES [J].
BERESIS, R ;
PANEK, JS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (08) :1609-1614
[2]  
CLARK TD, 1992, J ORG CHEM, V57, P4323
[3]   ALKENYL OXAZOLIDINONES BY STEREOSELECTIVE EPOXIDATION OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES - SYNTHESIS OF ANY ISOMER (RR, RS, SR OR SS, E OR Z) BEARING 1,4-RELATED CHIRAL CENTERS ACROSS A DOUBLE-BOND [J].
CLAYDEN, J ;
COLLINGTON, EW ;
LAMONT, RB ;
WARREN, S .
TETRAHEDRON LETTERS, 1993, 34 (13) :2203-2206
[4]   THE DIASTEREOSELECTIVITY OF ELECTROPHILIC ATTACK ON TRIGONAL CARBON ADJACENT TO A STEREOGENIC CENTER - DIASTEREOSELECTIVE ALKYLATION AND PROTONATION OF OPEN-CHAIN ENOLATES HAVING A STEREOGENIC CENTER CARRYING A SILYL GROUP AT THE BETA POSITION [J].
CRUMP, RANC ;
FLEMING, I ;
HILL, JHM ;
PARKER, D ;
REDDY, NL ;
WATERSON, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24) :3277-3294
[5]  
FLEMING I, 1992, J CHEM SOC PERK T 1, P3295, DOI 10.1039/p19920003295
[6]   THE STEREOCHEMISTRY OF THE REACTION OF ALLYLSILANES WITH OSMIUM-TETROXIDE AND OF THE EPOXIDATION AND METHYLENATION OF ALLYLSILANES [J].
FLEMING, I ;
LAWRENCE, NJ ;
SARKAR, AK ;
THOMAS, AP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24) :3303-3308
[7]   S(N)2' RING-OPENING OF AZIRIDINES BEARING AN ALPHA,BETA-UNSATURATED ESTER GROUP WITH ORGANOCOPPER REAGENTS - A NEW STEREOSELECTIVE SYNTHETIC ROUTE TO (E)-ALKENE DIPEPTIDE ISOSTERES [J].
FUJII, N ;
NAKAI, K ;
TAMAMURA, H ;
OTAKA, A ;
MIMURA, N ;
MIWA, Y ;
TAGA, T ;
YAMAMOTO, Y ;
IBUKA, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (11) :1359-1371
[8]  
GOSH AK, 1991, J ORG CHEM, V56, P6500
[9]   SYNTHESIS OF (E)-OLEFIN DIPEPTIDE ISOSTERES [J].
MCKINNEY, JA ;
EPPLEY, DF ;
KEENAN, RM .
TETRAHEDRON LETTERS, 1994, 35 (33) :5985-5988
[10]   ALLYLSILANES IN ORGANIC-SYNTHESIS - AN APPROACH TO THE STEREOSELECTIVE SYNTHESIS OF UNITS FOR NATURAL PRODUCT SYNTHESIS [J].
MURPHY, PJ ;
PROCTER, G .
TETRAHEDRON LETTERS, 1990, 31 (07) :1059-1062