Catalytic Asymmetric Halohydroxylation of α, β‐Unsaturated Ketones with Water as the Nucleophile. Issue 10 (16th April 2020)

• Record Type: Journal Article
• Authors: Li, Weiwei; Zhou, Pengfei; Li, Gonglin; Lin, Lili; Feng, Xiaoming
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 10(2020)
• Page Start: 1982
• Page End: 1987
• Publication Date: 2020-04-16
• Subjects: Asymmetric catalysis -- Halohydroxylation -- α, β-Unsaturated ketones -- Chiral N, N′-dioxide -- Water; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000080
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The catalytic asymmetric halohydroxylation of α, β‐unsaturated ketones with water as the nucleophile has been realized by applying a chiral N, N′ ‐dioxide/Fe(OTf)2 complex as the catalyst. Bromo‐, chloro‐ and iodo‐hydroxylations were all suitable in this catalytic system. A variety of α‐halo‐β‐hydroxy ketones were obtained in often good yields with generally high dr and ee values. Besides, a Michael/α‐halogenation process was considered more possible and a possible transition state model was proposed to explain the origin of stereoselectivity. Abstract :