Asymmetric Synthesis of Dihydronaphthalene‐1, 4‐Diones via Carbene‐Catalyzed Stereodivergent Reaction. Issue 17 (11th July 2019)

• Record Type: Journal Article
• Authors: Zhao, Zhifei; Yang, Shuang; Lan, Shouang; Liu, Jinggong; Liu, Shuhua; Fang, Xinqiang
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 17(2019)
• Page Start: 3943
• Page End: 3949
• Publication Date: 2019-07-11
• Subjects: umpolung -- cyclization -- carbene -- kinetic resolution; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900506
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 2‐Hydroxy‐2, 3‐dihydronaphthalene‐1, 4‐diones (HDNDs) are ubiquitous in natural products and bioactive molecules, but the rapid asymmetric construction of such scaffolds remains a significant challenge to date. Reported herein is the rapid construction of the above key units via carbene‐catalyzed benzoin reaction. The resolution technique of divergent reaction on racemic mixture (divergent RRM) was employed, affording both isomers of HDNDs in a one‐step fashion. Disubstituted substrates afford products with two contiguous quaternary stereocenters. A series of highly selective transformations on the products can be realized, and mechanistic studies indicate that the benzoin reaction is much faster than the racemization process and the aldol reaction. Abstract :