943599-16-4Relevant articles and documents
Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a: C -silyl latent pronucleophile
Zi, You,Lange, Markus,Vilotijevic, Ivan
supporting information, p. 5689 - 5692 (2020/06/19)
The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)-methyl)phosphonate reagent as a latent pronucleophile in the Lewis base catalyzed substitution of allylic fluorides. The reaction proceeds
Regioselective dehydroxytrifluoromethylthiolation of allylic and propargylic alcohols with AgSCF3
Liu, Yin-Li,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 953 - 956 (2019/03/07)
The reaction of easily available Morita–Baylis–Hillman (MBH) alcohols with AgSCF3 in the presence of n-Bu4NI and KI affords primary allylic SCF3 products in high yields and excellent regioselectivities. This regioselective dehydroxytrifluoromethylthiolation protocol could also be extended to propargylic alcohols for the preparation of the primary propargylic SCF3 products.
Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles
Zi, You,Lange, Markus,Schultz, Constanze,Vilotijevic, Ivan
supporting information, p. 10727 - 10731 (2019/07/09)
Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, i
Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties
Rasson, Corentin,Stouse, Adrien,Boreux, Arnaud,Cirriez, Virginie,Riant, Olivier
supporting information, p. 9234 - 9237 (2018/06/04)
Herein, we report the copper-catalyzed domino borylation/aldolisation of methyl 2-fluoroacrylate with carbonyl compounds followed by an elimination to give Morita–Baylis–Hillman (MBH) analogues. The optimal conditions described were shown to be compatible
Design, synthesis and evaluation of 3-arylidene azetidin-2-ones as potential antifungal agents against Alternaria solani Sorauer
Delong, Wang,Yongling, Wu,Lanying, Wang,Juntao, Feng,Xing, Zhang
, p. 6661 - 6673 (2017/11/17)
A new concise and facile method was explored to synthesize a collection of new 3-arylidene azetidin-2-ones, which could be regarded as the derivatives of the hybrid scaffold of bioactive natural cinnamamide and heterocycle azetidi-2-one. The structures of
A versatile approach to noncoded β-hydroxy-α-amino esters and α-amino acids/esters from morita-baylis-hillman adducts
Ullah, Hamid,Ferreira, Andr V.,Bendassolli, Jos A.,Rodrigues, Manoel T.,Formiga, Andr Luiz B.,Coelho, Fernando
supporting information, p. 113 - 123 (2015/02/02)
A simple and straightforward approach to the diastereoselective synthesis of noncoded β-hydroxy-α-amino esters from Morita-Baylis-Hillman (MBH) adducts is described. The strategy is based on a one-pot sequence involving an oxidative cleavage of the double bond of silylated Morita-Baylis-Hillman adducts, followed by the reaction with hydroxylamine hydrochloride/pyridine to form oximes. The stereoselective reduction of the oximes with the mixture MoCl5·nH2O/NaBH3CN led to the corresponding anti-β-hydroxy-α-amino esters in four steps in good overall yield and with diastereoselectivity higher than 95%. A slight modification of the synthetic approach has allowed for the racemic synthesis of a set of noncoded α-amino esters/acids and DOPA
1,1′-Carbonyldiimidazole mediates the synthesis of N-substituted imidazole derivatives from Morita-Baylis-Hillman adducts
Rodrigues Jr., Manoel T.,Santos, Marilia S.,Santos, Hugo,Coelho, Fernando
, p. 180 - 183 (2014/01/06)
In this Letter, we describe a simple and straightforward method for the synthesis of N-substituted imidazole derivatives. 1,1-carbonyldiimidazole mediates the process, which requires no activation group step. We obtained imidazole derivatives in high yiel
Heterocycles from Morita-Baylis-Hillman adducts: Synthesis of 5-oxopyrazolidines, arylidene-5-oxopyrazolidines, and oxo-2,5-dihydro-pyrazols
Correia, José Tiago M.,Rodrigues Jr., Manoel T.,Santos, Hugo,Tormena, Cláudio F.,Coelho, Fernando
, p. 826 - 832 (2013/07/25)
Starting from Morita-Baylis-Hillman (MBH) adducts, an approach for the synthesis of oxopyrazolidines, arylidene-oxopyrazolidines, and oxo-2,5-dihydropyrazoles is described. The method is based on a tandem process involving a Michael addition of amino-guan
Mapping the mechanism of nickel-ferrophite catalysed methylation of baylis-hillman-derived SN2′ electrophiles
Novak, Andrew,Calhorda, Maria Jose,Costa, Paulo Jorge,Woodward, Simon
supporting information; experimental part, p. 898 - 903 (2009/07/19)
Enantioselective Ni-catalysed methylation of Baylis-Hillman-derived allylic electrophiles in the presence of ferrophite ligands has been investigated computationally and experimentally. The sense and degree of enantioselectivity attained is independent of both the leaving group and the isomeric structure of the initial allylic halide. DFT studies support the selective formation of a limited number of energetically favoured anti and syn π-allyl intermediates. The observed regio- and enantioselectivity can be rationalised based on the energetics of these structures.
