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Diastereoselective Aldol Reaction of α‐Azido Ketones with α‐CF3 Pyruvate to Organoazides with Vicinal Tetrasubstituted Carbons
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2024-05-03 , DOI: 10.1002/ejoc.202400348
Yang Gao 1 , Xue-Xin Zhang 1 , Zhi Tu 1 , Jin-Sheng Yu 1 , Jian Zhou 2
Affiliation  

A direct diastereoselective aldol reaction of cyclic or acyclic α‐azido ketones with α‐trifluoromethyl (CF3) pyruvate catalysed by DABCO is developed, which allowed the facile access of CF3‐containing multifunctional organoazides with vicinal tetrasubstituted carbons in good to high yields and diastereoselectivities. Moreover, phenylethynyl trifluoro‐ and difluoromethyl ketones are also viable substrates. Up to 50% enantioselectivity could be obtained in the initial exploration of the catalytic asymmetric variant.

中文翻译:

α-叠氮酮与 α-CF3 丙酮酸的非对映选择性羟醛反应生成邻位四取代碳的有机叠氮化物

开发了由 DABCO 催化的环状或无环 α-叠氮酮与 α-三氟甲基 (CF3) 丙酮酸的直接非对映选择性羟醛反应,该反应允许以良好至高的产率和非对映选择性轻松获得具有邻位四取代碳的含 CF3 多功能有机叠氮化物。此外,苯乙炔基三氟和二氟甲基酮也是可行的底物。在催化不对称变体的初步探索中可以获得高达 50% 的对映选择性。
更新日期:2024-05-03
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