Diastereoselective intramolecular α-amidoalkylation reactions of L-DOPA derivatives.: Asymmetric synthesis of pyrrolo[2,1-a]isoquinolines

被引：48

作者：

García, E ^{[1
]}

Arrasate, S ^{[1
]}

Lete, E ^{[1
]}

Sotomayor, N ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencia & Tecnol, Dept Quim Organ 2, Bilbao 48080, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 25期

关键词：

D O I：

10.1021/jo051584w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).

引用

页码：10368 / 10374

页数：7