Stereoselective Divergent Synthesis of Chiral Pyrazolone Derivatives via Multicomponent Cascade Reactions by Isothiourea Catalysis

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-26 DOI:10.1021/acs.orglett.4c04395

Xin Liu, Siyi Chen, Jun Huang, Peiyao Liang, Liejin Zhou, Shoulei Wang

引用次数: 0

Abstract

Isothiourea-catalyzed multicomponent cascade reactions are challenging due to the existence of competitive side reactions between multiple reaction partners and intermediates. Herein, we report a practical and efficient protocol for the stereoselective divergent synthesis of pyrazolone-derived β-amino acid esters and β-lactams by isothiourea catalysis. Two distinct reaction pathways are identified, which are controlled by esterification or lactamization of the zwitterionic intermediate. The strategy is attractive because of the convenient one-step procedure, mild conditions, high stereoselectivity, and good functional-group tolerance.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.