501098-87-9Relevant articles and documents
Chiral β-Keto Propargylamine Synthesis via Enantioselective Mannich Reaction of Enamides with C-Alkynyl N-Boc N, O-Acetals
Feng, Fang-Fang,Li, Shen,Cheung, Chi Wai,Ma, Jun-An
, p. 8419 - 8423 (2019)
Propargylamines are an important class of compounds in organic synthesis and drug discovery, yet the synthesis of chiral β-keto propargylamines remains underdeveloped. Herein, we describe a streamlined and general enantioselective Mannich reaction of enamides with C-alkynyl N-Boc N,O-acetals, which serve as readily available C-alkynyl imine precursors, to access a broad range of chiral β-keto N-Boc-propargylamines bearing single stereogenic centers in high yields (up to 98%) and in high enantioselectivities (up to 95% ee).
NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenonesviaα,β-unsaturated acyl azoliums
Dzieszkowski, Krzysztof,S?otwiński, Micha?,Rafińska, Katarzyna,Muzio?, Tadeusz M.,Rafiński, Zbigniew
supporting information, p. 9999 - 10002 (2021/10/06)
A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenesviathe formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.
Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes
Liu, Zheng-Li,Yang, Chao,Xue, Qi-Yan,Zhao, Meng,Shan, Cui-Cui,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 16538 - 16542 (2019/11/11)
A copper-catalyzed silylation of propargyl dichlorides was developed to access chloro-substituted allenylsilanes under mild reaction conditions. Moreover, enantioenriched chloro-substituted allenylsilanes can be synthesized in moderate to high yields and good enantioselectivities with this protocol.