Direct coupling of pyrroles with carbonyl compounds: Short enantioselective synthesis of (S)-Ketorolac

被引：150

作者：

Baran, PS ^{[1
]}

Richter, JM ^{[1
]}

Lin, DW ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 04期

关键词：

C-C coupling; copper; enantioselectivity; heterocycles; total synthesis;

D O I：

10.1002/anie.200462048

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An odd couple: The union of pyrroles and carbonyl compounds (ketones, amides, esters, lactones, lactams, see scheme) is described, and by the use of an intramolecular variant of this new method, the nonsteroidal, anti-inflammatory drug (S)-ketorolac has been prepared in a short enantioselective synthesis. Mechanistic underpinnings of this reaction, which couples unfunctionalized C(sp2) and C(sp3) atoms, are also discussed.

引用

页码：609 / 612

页数：4

共 31 条

[1]

[Anonymous], 1991, Comprehensive Organic Synthesis

[2]

[Anonymous], 2002, J ORGANOMET CHEM

[3] The chemistry of pentavalent organobismuth reagents .14. Recent advances in the copper-catalyzed phenylation of amines. [J].