Novel Supramolecular Palladium Catalyst for the Asymmetric Reduction of Imines in Aqueous Media

被引：77

作者：

da Silva, Wender A. ^{[2
,3
]}

Rodrigues, Manoel T., Jr. ^{[1
]}

Shankaraiah, N. ^{[2
]}

Ferreira, Renan B. ^{[1
]}

Andrade, Carlos Kleber Z. ^{[3
]}

Pilli, Ronaldo A. ^{[1
]}

Santos, Leonardo S. ^{[2
]}

机构：

[1] Univ Estadual Campinas, Inst Chem, Campinas, Brazil

[2] Univ Talca, Lab Asymmetr Synth, Chem Inst Nat Resources, Talca, Chile

[3] Univ Brasilia, Inst Chem, Brasilia, DF, Brazil

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

基金：

巴西圣保罗研究基金会;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; BETA-CYCLODEXTRIN; TRANSFER HYDROGENATION; NEW-CALEDONIA; COMPLEXES; ALKALOIDS; DEPLANCHEINE; KETONES; CARBOLINE; PLANTS;

D O I：

10.1021/ol9011772

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach to the asymmetric reduction of dihydro-p-carboline derivatives to the corresponding tetrahydro-beta-carbolines is described based on the supramolecular lyophilized complex formed from beta-cyclodextrin/imines as an enzyme mimetic and palladium hydride as the reducing agent. The methodology allowed us to develop a short and efficient preparation of (R)-harmicine and (R)-deplancheine alkaloids in high overall yields and ee of 89 and 90%, respectively.

引用

页码：3238 / 3241

页数：4

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