Cooperative Pd/Chiral Secondary Amine Enabled Diastereo- and Enantioselective [3 + 2] Cycloannulation: Synthesis of Polysubstituted Cyclopentanes.

• Tác giả: Limei Gao, Dongqing He, Jikai Liu, Zuoqin Luo, Yuting Tian, Yongsheng Zheng
• Ngôn ngữ: eng
• Ký hiệu phân loại: 296.1146 Sources
• Thông tin xuất bản: United States : Organic letters , 2025
• Bộ sưu tập: NCBI
• ID: 183774

Tóm tắt

A cooperative palladium/chiral amine enabled diastereo- and enantioselective [3 + 2] cycloaddition of π-allyl 1,3-dipoles with α,β-unsaturated aldehydes has been developed. A series of highly functionalized cyclopentanes bearing three continuous tertiary stereocenters can be facilely and efficiently obtained in good to excellent yields (51-97%) with synthetically useful diastereo- and enantioselectivity (93-99% ee) under mild reaction conditions. Control experiments and HRMS analyses were conducted to elucidate the possible mechanism. The utility of the current method was demonstrated by the gram-scale synthesis and elaboration of the products into various functionalized cyclopentanes.