Polystyrene-supported organocatalysts for α-selenenylation and Michael reactions A common post-modification approach for catalytic differentiation

被引：24

作者：

Giacalone, Francesco ^{[1
]}

Gruttadauria, Michelangelo ^{[1
]}

Agrigento, Paola ^{[1
]}

Campisciano, Vincenzo ^{[1
]}

Noto, Renato ^{[1
]}

机构：

[1] Univ Palermo, Sez Chim Organ E Paterno, Dipartimento Sci & Tecnol Mol & Biomol STEMBIO, I-90128 Palermo, Italy

来源：

CATALYSIS COMMUNICATIONS | 2011年 / 16卷 / 01期

关键词：

Organocatalysis; Supported catalysts; Michael reaction; alpha-selenenylation; RECYCLABLE CATALYST; PROLINE; ALDEHYDES; NITROOLEFINS; STRATEGY; WATER;

D O I：

10.1016/j.catcom.2011.08.040

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Three different resin-supported catalysts have been prepared by using the well established post-modification approach by means of thiol-ene coupling reaction. Two catalysts were tested for the first time in the asymmetric alpha-selenenylation of propanal, while the third catalyst was used in the Michael addition reaction. While the preliminary results are not encouraging in the case of supported Jorgensen' catalyst, interesting data have been collected with both for the supported MacMillan and prolyl-prolinol catalysts. In fact, these catalysts displayed good activity and selectivity. A reversed enantioselectivity in the alpha-selenenylation was observed by changing the polarity of the solvent. Finally, these materials were easily recovered, and used four and five times, respectively. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：75 / 80

页数：6

共 23 条

[1] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B [J].