A HIGHLY STEREOSELECTIVE SYNTHESIS OF (E)-ALKENE DIPEPTIDE ISOSTERES VIA ORGANOCYANOCOPPER - LEWIS ACID MEDIATED REACTION

被引：170

作者：

IBUKA, T ^{[1
]}

HABASHITA, H ^{[1
]}

OTAKA, A ^{[1
]}

FUJII, N ^{[1
]}

OGUCHI, Y ^{[1
]}

UYEHARA, T ^{[1
]}

YAMAMOTO, Y ^{[1
]}

机构：

[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 14期

关键词：

D O I：

10.1021/jo00014a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.

引用

页码：4370 / 4382

页数：13

共 150 条

[1]

AHN NT, 1980, TOP CURR CHEM, V88, P144

[2] ORGANOCOPPER CONJUGATE ADDITION-REACTION IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].