Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable Diastereoselectivity

Anton A Nechaev; Kristof Van Hecke; Manzoor Zaman; Stepan Kashtanov; Liviu Ungur; Olga P Pereshivko; Vsevolod A Peshkov; Erik V Van der Eycken

doi:10.1021/acs.joc.8b00953

Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable Diastereoselectivity

J Org Chem. 2018 Aug 3;83(15):8170-8182. doi: 10.1021/acs.joc.8b00953. Epub 2018 Jul 11.

Authors

Anton A Nechaev¹, Kristof Van Hecke², Manzoor Zaman³, Stepan Kashtanov⁴, Liviu Ungur⁵, Olga P Pereshivko³, Vsevolod A Peshkov³, Erik V Van der Eycken^{1

6}

Affiliations

¹ Laboratory of Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry , University of Leuven (KU Leuven) , Celestijnenlaan 200F , B-3001 Leuven , Belgium.
² XStruct, Department of Chemistry , Ghent University , Krijgslaan 281-S3 , B-9000 Ghent , Belgium.
³ College of Chemistry, Chemical Engineering and Materials Science , Soochow University , Dushu Lake Campus , Suzhou 215123 , China.
⁴ Institute of Functional Nano & Soft Materials (FUNSOM) and Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices , Soochow University , Suzhou 215123 , China.
⁵ Theory of Nanomaterials Group, Department of Chemistry , University of Leuven (KU Leuven) , Celestijnenlaan 200F , B-3001 Leuven , Belgium.
⁶ Peoples' Friendship University of Russia (RUDN University) , Miklukho-Maklaya Street 6 , Moscow 117198 , Russia.

PMID: 29966417
DOI: 10.1021/acs.joc.8b00953

Abstract

A gold-catalyzed post-Ugi ipso-cyclization for the diastereoselective synthesis of spirocyclic pyrrol-2-one-dienone system is described. Tuning the catalytic system, solvent, and temperature allowed selectively attaining two sets of diastereoisomers. The scope of the process has been evaluated, and a putative mechanistic model was proposed.