Hydrogen-Borrowing-Based Methods for the Construction of Quaternary Stereocentres.

• Tác giả: Jessica L Crompton, Timothy J Donohoe, Timothy C Jenkins, Sam M Rowe
• Ngôn ngữ: eng
• Thông tin xuất bản: Germany : Angewandte Chemie (International ed. in English) , 2025
• Bộ sưu tập: NCBI
• ID: 176541

Tóm tắt

Compounds containing quaternary stereocentres are a valuable motif in biologically active compounds. Herein we present our strategy to utilise the hydrogen borrowing manifold to access α-quaternary ketones via a tandem acceptorless dehydrogenation-cyclisation cascade. This new application of the methodology results in the formation of five- and six-membered carbocycles with a high degree of diastereoselectivity. Interestingly, benzylic alcohol substrates behaved anomalously and eliminated sulfinate in situ to give a set of rearranged α-quaternary ketone products.