Enantioselective Ring Opening of Azetidines via Charge Recognition in Hydrogen-Bond-Donor Catalysis.

• Tác giả: Joseph J Gair, Mayuko Isomura, Eric N Jacobsen, Daniel A Strassfeld, Corin C Wagen
• Ngôn ngữ: eng
• Ký hiệu phân loại: 606 Organizations
• Thông tin xuất bản: United States : Journal of the American Chemical Society , 2025
• Bộ sưu tập: NCBI
• ID: 180379

Tóm tắt

We report the highly enantioselective ring-opening of 3-substituted azetidines by alkyl and acyl halides promoted by a chiral squaramide hydrogen-bond donor catalyst. Broad scope is achieved across a variety of substrate combinations possessing disparate steric features. The same catalyst had been identified previously to promote enantioselective opening of oxetanes via both Lewis and Brønsted acid mechanisms. This remarkable generality is interpreted to arise from catalyst recognition of the conserved electrostatic features of the dipolar enantioselectivity-determining transition states in the ring-opening S