1803239-44-2Relevant academic research and scientific papers
α-Functionalization of 2-Vinylpyridines via a Chiral Phosphine Catalyzed Enantioselective Cross Rauhut-Currier Reaction
Qin, Cong,Liu, Yonghai,Yu, Yang,Fu, Yiwei,Li, Hao,Wang, Wei
, p. 1304 - 1307 (2018)
Herein, 2-vinylpyridines as a new type of electron-poor system for the asymmetric cross Rauhut-Currier reaction are reported. 2-Vinylpyridines are chemo- and enantioselectively activated by a newly designed chiral phosphine catalyst. The new reaction provides a powerful synthetic tool for accessing structurally diverse, highly valued chiral pyridine building blocks in good yields and with high enantioselectivities. Preliminary mechanistic studies reveal that two NH protons in the catalyst are critical for the synergistic activation of the substrates and governing the stereoselectivity of this reaction.
Chiral sulfinamide bisphosphine catalysts: Design, synthesis, and application in highly enantioselective intermolecular cross-Rauhut-Currier reactions
Zhou, Wei,Su, Xiao,Tao, Mengna,Zhu, Chaoze,Zhao, Qingjie,Zhang, Junliang
, p. 14853 - 14857 (2015)
A novel type of highly efficient chiral sulfinamide bisphosphine catalysts (Wei-Phos) were developed. These could be easily prepared from commercially available starting materials. Wei-Phos has shown good performance in the very challenging intermolecular cross-Rauhut-Currier reactions of vinyl ketones and 3-acyl acrylates or 2-ene-1,4-diones, leading to the R-C products in high yields with up to 99 % ee under 2.5-5 mol% catalyst loading. The highly regio- and enantio-selective cross-Rauhut-Currier reactions of 2-ene-1,4-diones and vinyl ketone have yet reported so far. Highly efficient chiral sulfinamide bisphosphine catalysts (Wei-Phos, 1) were developed that could be easily prepared from commercially available starting materials. Wei-Phos has shown good performance in the intermolecular cross-Rauhut-Currier reactions of vinyl ketones and 3-acyl acrylates or 2-ene-1,4-diones, leading to products in high yields with up to 99 % ee under 2.5-5.0 mol% catalyst loading.
A hand [...] compound and its full configuration, its preparation method and application
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, (2018/05/16)
The invention provide a preparation method for a chiral tertiary phosphine compound containing chiral sulfonamide and shown as formula (1). The method takes aldehyde (ketone) 2 and chiral sulfinamide 3 as raw materials, which react with a nucleophilic rea
Functionalized Tetrahydropyridines by Enantioselective Phosphine-Catalyzed Aza-[4 + 2] Cycloaddition of N-Sulfonyl-1-aza-1,3-dienes with Vinyl Ketones
Wang, Huamin,Zhou, Wei,Tao, Mengna,Hu, Anjing,Zhang, Junliang
supporting information, p. 1710 - 1713 (2017/04/11)
The development of electron-demand disfavored [4 + 2] cycloaddition of two electron-deficient reacting partners poses a considerable challenge. An enantioselective aza-[4 + 2] cycloaddition of electron-deficient N-sulfonyl-1-aza-1,3-dienes is possible with vinyl ketones via phosphine catalysis, which provides facile access to a wide range of enantioenriched trifluoromethylated tetrahydropyridines in up to 97% yield with 97% ee and >20:1 dr. The mechanistic study indicated that this cycloaddition proceeds via a tandem intermolecular aza-Rauhut-Currier/intramolecular aza-Michael addition reaction.
Novel chiral sulfinamide phosphines: Valuable precursors to chiral β-aminophosphines
Chen, Peng,Su, Xiao,Zhou, Wei,Xiao, Yuanjing,Zhang, Junliang
, p. 2700 - 2706 (2016/05/10)
Starting from commercially available aldehyde and chiral tert-butanesulfinamide, a series of chiral sulfinamide phosphines (Xiao-Phos) were synthesized via a two-step condensation-nucleophilic addition procedure. In most cases, nucleophilic addition of th
Design, synthesis, and application of a chiral sulfinamide phosphine catalyst for the enantioselective intramolecular rauhut-currier reaction
Su, Xiao,Zhou, Wei,Li, Yangyan,Zhang, Junliang
supporting information, p. 6874 - 6877 (2015/06/02)
A novel class of chiral sulfinamide phosphine catalysts (Xiao-Phos) are reported, which can be easily prepared from inexpensive commercially available starting materials. The Xiao-Phos catalysts showed good performance in enantioselective intramolecular R
