Asymmetric Intramolecular C-H Insertion of α-Diazoacetamides in Water by Dirhodium(II) Catalysts Derived from Natural Amino Acids

被引：26

作者：

Candeias, Nuno R. ^{[1
,2
]}

Carias, Carolina ^{[3
,4
]}

Gomes, Luis F. R. ^{[3
,4
]}

Andre, Vania ^{[5
]}

Teresa Duarte, M. ^{[5
]}

Gois, Pedro M. P. ^{[1
]}

Afonso, Carlos A. M. ^{[1
,3
,4
]}

机构：

[1] Univ Lisbon, Fac Farm, IMed UL, P-1649003 Lisbon, Portugal

[2] Tampere Univ Technol, Dept Chem & Bioengn, FIN-33101 Tampere, Finland

[3] Univ Lisbon, Ctr Quim Fis Mol, CQFM, P-1049001 Lisbon, Portugal

[4] Univ Lisbon, IN Inst Nanosci & Nanotechnol, P-1049001 Lisbon, Portugal

[5] Inst Super Tecn, CQE Ctr Quim Estrutural, P-1049001 Lisbon, Portugal

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 16期

关键词：

C-H insertion; alpha-diazo compounds; dirhodium(II); ss-lactams; water; BETA-KETO-ESTERS; CATIONIC CARBOXYLATO COMPLEXES; RHODIUM CARBENOIDS; ORGANIC-SYNTHESIS; DIAZO-COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; DIAZOCARBONYL COMPOUNDS; CHIRAL CATALYSTS; OXO THIOETHERS; CYCLOPROPANATION;

D O I：

10.1002/adsc.201200101

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The asymmetric dirhodium(II)-catalyzed intramolecular C-H insertion of alpha-diazo acetamides in water is described for the first time. The use of natural alpha-amino acids as chiral ligands allowed the preparation of novel dirhodium(II) homochiral complexes by a simple procedure consisting of the in situ ligand exchange starting from dirhodium tetraacetate. The catalytic system was further reused up to 7 cycles and beta-lactams were obtained in good yields and enantiomeric excess.

引用

页码：2921 / 2927

页数：7

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