A polystyrene-supported 9-amino(9-deoxy)epi quinine derivative for continuous flow asymmetric Michael reactions

被引：47

作者：

Izquierdo, Javier ^{[1
]}

Ayats, Carles ^{[1
]}

Henseler, Andrea H. ^{[1
]}

Pericas, Miquel A. ^{[1
,2
]}

机构：

[1] Inst Chem Res Catalonia ICIQ, E-43007 Tarragona, Spain

[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 14期

关键词：

PHASE-TRANSFER CATALYSTS; CINCHONA ALKALOID DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; ALPHA-NITROACETATE; AMMONIUM-SALTS; IMMOBILIZATION; ORGANOCATALYST; CHEMISTRY; KETONES;

D O I：

10.1039/c5ob00325c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A polystyrene (PS)-supported 9-amino(9-deoxy)epi quinine derivative catalyzes Michael reactions affording excellent levels of conversion and enantioselectivity using different nucleophiles and structurally diverse enones. The highly recyclable, immobilized catalyst has been used to implement a single-pass, continuous flow process (residence time: 40 min) that can be operated for 21 hours without significant decrease in conversion and with improved enantioselectivity with respect to batch operation. The flow process has also been used for the sequential preparation of a small library of enantioenriched Michael adducts.

引用

页码：4204 / 4209

页数：6

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