EPC SYNTHESIS OF 5-SUBSTITUTED 2-OXO-CYCLOPENTANECARBOXYLATES VIA CONJUGATE ADDITION OF CUPRATES TO ASYMMETRIC SHIELDED 2-OXO-CYCLOPENTENECARBOXYLATES

被引：10

作者：

URBAN, E ^{[1
]}

KNUHL, G ^{[1
]}

HELMCHEN, G ^{[1
]}

机构：

[1] UNIV HEIDELBERG, INST ORGAN CHEM, D-69120 HEIDELBERG, GERMANY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 40期

关键词：

D O I：

10.1016/0040-4039(95)01537-R

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric shielded 2-oxo-cyclopentenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclopentanecarboxylate 2 with camphor derived concave alcohols 1n and 1x and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 degrees C and deprotection by ethanolysis gave enantiomerically pure 5-substituted 2-oxo-cyclopentanecarboxylates 13-18 and ent-13-18, valuable as chiral building blocks in natural product synthesis.

引用

页码：7229 / 7232

页数：4