手性有机催化异噁唑-5(4)-酮与色酮衍生的亚胺的对映选择性曼尼希反应。

Organocatalytic enantioselective Mannich reaction of isoxazol-5(4)-ones to isatin-derived ketimines.

机构信息

Departament de Química Orgànica, Facultat de Química, Universitat de València, 46100-Burjassot, Spain.

出版信息

Org Biomol Chem. 2022 Nov 9;20(43):8395-8399. doi: 10.1039/d2ob01692c.

DOI:10.1039/d2ob01692c

Abstract

An efficient organocatalytic asymmetric Mannich reaction between isoxazol-5(4)-ones and isatin-derived ketimines has been developed. A bifunctional squaramide/Brønsted base organocatalyst catalyzed the enantioselective Mannich addition to afford chiral 3-aminooxindoles bearing a tetrasubstituted stereocenter at C3 decorated with an isoxazole moiety in good yields and with excellent enantioselectivities. Additionally, several synthetic transformations were described showing the versatility of the prepared compounds.

摘要

已开发出一种高效的异恶唑-5(4)-酮和色酮衍生的亚胺酮之间的手性有机催化不对称曼尼希反应。双功能酰亚胺/布朗斯台德碱有机催化剂催化对映选择性曼尼希加成，以高收率和优异的对映选择性得到在 C3 位带有四取代立体中心的手性 3-氨基氧吲哚，其中带有异恶唑部分。此外，还描述了几种合成转化，展示了所制备化合物的多功能性。

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