Asymmetric 1, 6‐Conjugate Addition of para‐Quinone Methides for the Synthesis of Chiral β, β‐Diaryl‐α‐Hydroxy Ketones. Issue 1 (15th November 2017)

• Record Type: Journal Article
• Authors: Gao, Yuan‐Yuan; Hua, Yuan‐Zhao; Wang, Min‐Can
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 1(2018)
• Page Start: 80
• Page End: 85
• Publication Date: 2017-11-15
• Subjects: asymmetric 1, 6-conjugated addition -- para-quinone methides -- chiral β, β-diaryl-α-hydroxy ketones -- dinuclear zinc-ProPhenol complexes; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700947
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A direct asymmetric 1, 6‐conjugated addition of α ‐hydroxy ketone to para ‐quinone methides has been developed. It is an efficient approach to the synthesis of chiral β, β ‐diaryl‐ α ‐hydroxy ketones. The reaction runs smoothly in the presence of ZnEt2 and nonracemic bis(diarylhydroxymethylpyrrolidinylmethyl)phenols (ProPhenols), and the desired products are obtained in good yields (up to 88%) and with high stereoselectivity (up to >99% ee and up to >99:1 dr). This reaction also can be run on a gram scale without impacting its enantioselectivity. Abstract :