醛和酮与聚合物负载有机催化剂的高度对映选择性α-氨氧基化反应。

Highly enantioselective alpha-aminoxylation of aldehydes and ketones with a polymer-supported organocatalyst.

作者信息

Font Daniel, Bastero Amaia, Sayalero Sonia, Jimeno Ciril, Pericàs Miquel A

机构信息

Institute of Chemical Research of Catalonia, Av Països Catalans, 16, Tarragona, Spain, and Departament de Química Orgànica, Universitat de Barcelona, Barcelona, Spain.

出版信息

Org Lett. 2007 May 10;9(10):1943-6. doi: 10.1021/ol070526p. Epub 2007 Apr 17.

DOI:10.1021/ol070526p

PMID:17439136

Abstract

The first catalytic enantioselective alpha-aminoxylation of aldehydes and ketones using an insoluble, polymer-supported organocatalyst (1) derived from trans-4-hydroxyproline is reported (ee: 96-99%). Reaction rates in the aminoxylation of cyclic ketones with 1 are higher than those reported with l-proline. The insoluble nature of 1 simplifies workup conditions and allows catalyst recycling without an apparent decrease in enantioselectivity or yield.

摘要

报道了使用一种由反式-4-羟基脯氨酸衍生的不溶性聚合物负载有机催化剂（1）对醛和酮进行首例催化对映选择性α-氨基氧基化反应（对映体过量值：96-99%）。用1对环酮进行氨基氧基化反应的速率高于用L-脯氨酸报道的反应速率。1的不溶性简化了后处理条件，并能使催化剂循环使用，而对映选择性或产率没有明显降低。