56750-80-2Relevant academic research and scientific papers
Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines
Luo, Xiaosheng,Wang, Ping
supporting information, p. 4960 - 4965 (2021/07/20)
Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.
Enantioselective Cyanosilylation of α,α-Dialkoxy Ketones by Using Phosphine-Thiourea Dual-Reagent Catalysis
Yu, Qi-Wen,Wu, Lu-Ping,Kang, Tian-Chen,Xie, Jin,Sha, Feng,Wu, Xin-Yan
supporting information, p. 3992 - 3996 (2018/07/31)
The first highly enantioselective cyanosilylation of α,α-dialkoxy ketones enabled by a dual-reagent catalysis has been developed. With the combination of a chiral bifunctional phosphine-thiourea and methyl acrylate, the key organophosphorus zwitterion intermediate was generated in situ as a novel Lewis base, which catalyzed the enantioselective cyanosilylation reaction in excellent yields (up to 99 %) with good-to-excellent enantioselectivities (up to 94 % ee).
Organocatalytic Enantioselective Acyloin Rearrangement of α-Hydroxy Acetals to α-Alkoxy Ketones
Wu, Hua,Wang, Qian,Zhu, Jieping
supporting information, p. 5858 - 5861 (2017/05/12)
We report an unprecedented organocatalytic enantioselective acyloin rearrangement of α,α-disubstituted α-hydroxy acetals. In the presence of a catalytic amount of chiral binol-derived N-triflyl phosphoramide, α-hydroxy acetals rearranged to α-alkoxy ketones in good to high yields with high enantioselectivities. Formation of an ion pair between the in situ generated oxocarbenium ion and the chiral phosphoramide anion was proposed to be responsible for the highly efficient transfer of chirality. Conditions for removal of cyclohexyl and cyclopentyl groups from the corresponding α-alkoxy ketones were uncovered underpinning their potential general utility as hydroxy protecting groups. Conversion of the rearranged products to the enantioenriched α-hydroxy ketone, 1,2-diol, β-amino alcohol and 1,4-dioxane was also documented.
Rh-catalyzed asymmetric hydrogenation of racemic aldimines via dynamic kinetic resolution
Fan, Dongyang,Lu, Jian,Liu, Yang,Zhang, Zhenfeng,Liu, Yangang,Zhang, Wanbin
, p. 5541 - 5547 (2016/08/05)
Catalyzed by a rhodium complex of P-stereogenic diphosphine ligand trichickenfootphos (TCFP), asymmetric hydrogenation of racemic aldimines via dynamic kinetic resolution has been realized for the preparation of chiral arylglycines with good yields and enantioselectivities.
Unexplored reactivity of 2-oxoaldehydes towards Pictet-Spengler conditions: Concise approach to β-carboline based marine natural products
Battini, Narsaiah,Padala, Anil K.,Mupparapu, Nagaraju,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
, p. 26258 - 26263 (2014/07/08)
Novel reactions under Pictet-Spengler conditions between tryptophan methyl ester/tryptamine and 2-oxoaldehydes have been developed and successfully utilized for the total synthesis of Merinacarboline (A and B), Eudistomin Y1, Pityriacitrin B, Pityriacitrin, Fascaplysin and analogues.
Versatile synthesis of 2-(substituted phenyl)-6,7-dihydro-1H-indol-4(5H)- ones from Morita-Baylis-Hillman acetates of 2-oxo-2-(substituted phenyl)acetaldehyde
Batchu, Harikrishna,Batra, Sanjay
experimental part, p. 2935 - 2944 (2012/06/29)
A versatile synthesis of 2-(substituted phenyl)-6,7-dihydro-1H-indol-4(5H)- ones from adducts of the Morita-Baylis-Hillman reaction between 2-oxo-2-(substituted phenyl)acetaldehydes and cyclohex-2-enone under mild conditions is described. Application of adducts prepared by the Morita-Baylis-Hillman reaction between 2-oxo-2-(substituted phenyl)acetaldehydes and cyclohex-2-enone for the synthesis of 2-(substituted phenyl)-6,7-dihydro- 1H-indol-4(5H)-ones has been described. Copyright
A New Synthetic Route to Aromatic Gyloxals
Mahato, S. B.,Podder, G.,Maitra, S. K.
, p. 1263 (2007/10/02)
Dichloroacylation of toluene, o- and m- xylenes, chloro- and bromo-benzenes and m-chlorotoluene under Friedel-Crafts conditions leads to the corresponding chloroketones (Ia-f) which on controlled hydrolysis afford the glyoxals (IIa-f) respectively.
SYNTHESIS OF METHYL-SUBSTITUTED INDENOQUINOLINES, INDENOQUINOXALINES, AND THEIR KETO DERIVATIVES AND INVESTIGATION OF THEIR STRUCTURES
Prostakov, N. S.,Pleshakov, V. G.,Abedin, Md. Zainul,Kordova, I. R.,Zakharov, V. F.,Zvolinskii, V. P.
, p. 556 - 566 (2007/10/02)
A series of difficultly obtainable and previously unknown methyl homologs of 11H-indenoquinoline, 11H-indenoquinoxaline, and the corresponding 11-keto derivatives were synthesized by new convenient methods, and their structures were investigated.By PMR with lanthanide shift reagents Eu(dpm)3, Pr(dpm)3 and Yb(dpm)3 it was established that the indenoquinolines and ketoindenoquinoxalines do not coordinate with any of the indicated reagents, while the 11-keto derivatives of the indenoquinolines, like those of the indenoquinoxalines, only enter coordination with Yb(dpm)3 at the oxygen atom in the case of the ketoindenoqui nolines and at the N10 nitrogen atom in the case of the indenoquinoxalines.The results from quantum-chemical calculations on the keto derivatives of the indenoquinoline and indenoquinoxaline series are given, and the reasons for the various directions of coordination of Yb(dpm)3 with this type of compound are discussed.
