133181-02-9Relevant academic research and scientific papers
Enantioselective allylic substitution of Morita-Baylis-Hillman adducts catalyzed by planar chiral [2.2]paracyclophane monophosphines
Zhang, Tang-Zhi,Dai, Li-Xin,Hou, Xue-Long
, p. 1990 - 1994 (2007)
Planar chiral [2,2]cyclophane monophosphines are efficient catalyst in the reaction of Morita-Baylis-Hillman adducts with phthalimide. The corresponding allylic substituted products were afforded in high yields and in good to moderate ee.
Highly diastereoselective Diels-Alder reactions of Baylis-Hillman adducts
Aggarwal, Varinder K.,Patin, Amaury,Tisserand, Steve
, p. 2555 - 2557 (2005)
(Chemical Equation Presented) Baylis-Hillman adducts were found to be excellent dienophiles in Diels-Alder reactions, providing essentially complete diastereocontrol (although mixtures of endo/exo isomers) with all dienes.
A new route to substituted glutaric acid derivatives from allylic malonates
Mason,Emslie,Drewes
, p. 183 - 190 (1995)
A new, high yielding route to substituted glutaric acid derivatives via anester enolate Claisen rearrangement of allylic malonates is described.
HIGH-PRESSURE INITIATED SYNTHESIS OF DOMINICALURES 1 AND 2 BY THE BAYLIS-HILLMAN METHOD
Moiseenkov, A. M.,Cheskis, B. A.,Shpiro, N. A.,Stashina, G. A.,Zhulin, V. M.
, p. 517 - 521 (1990)
The dimerization of methyl acrylate to dimethyl α-methyleneglutarate by the action of tributylphosphine in the absence of a solvent was investigated.Methyl α-methylene-β-hydroxypentanoate was obtained with a moderate yield by the condensation of propionaldehyde with methyl acrylate catalyzed by triphenylphosphine or 1,4-diazabicyclooctane and initiated by high pressure.In the last of these data a three-stage stereospecific synthesis of dominicalures 1 and 2 (components of the aggregation pheromone of the grain beetle) was realized from sec-amyl acrylate and propionaldehyde or isobutyraldehyde.
The asymmetric Baylis-Hillman reaction as a template in organic synthesis
Brzezinski, Linda Joy,Rafel, Sara,Leahy, James W.
, p. 16423 - 16434 (1997)
The Bayils-Hillman reaction of camphor-based acrylates has been demonstrated to result in the formation of products with high optical purity. A model that explains these results and the use of these products in the formation of anti aldol adducts is discu
Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS)
Barcelos, Rosimeire C.,Zeoly, Lucas A.,Rodrigues, Manoel T.,Ferreira, Bruno R. V.,Eberlin, Marcos N.,Coelho, Fernando
, p. 1557 - 1570 (2015/02/19)
Abstract We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to goo
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
Highly efficient synthesis of novel Morita-Baylis-Hillman adducts from activated ketones using a DABCO-based hydroxy ionic liquid (HIL) as a recyclable catalyst-solvent
Khalafi-Nezhad, Ali,Mohammadi, Somayeh
experimental part, p. 1725 - 1735 (2012/07/01)
A highly efficient non-imidazolium DABCO-based ionic liquid has been prepared for the synthesis of biologically active Morita-Baylis-Hillman adducts from activated ketones. The results show that the ionic liquid is very efficient in the Morita-Baylis-Hill
Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water
Zhu, Bo,Yan, Lin,Pan, Yuanhang,Lee, Richmond,Liu, Hongjun,Han, Zhiqiang,Huang, Kuo-Wei,Tan, Choon-Hong,Jiang, Zhiyong
experimental part, p. 6894 - 6900 (2011/10/09)
A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using 18O-labeling experiments.
Hyphenating the curtius rearrangement with morita-baylis-hillman adducts: Synthesis of biologically active acyloins and vicinal aminoalcohols
Amarante, Giovanni W.,Cavallaro, Mayra,Coelho, Fernando
experimental part, p. 1568 - 1584 (2011/11/06)
Using Morita-Baylis-Hillman adducts as substrates, the Curtius rearrangement was performed in a sequence that allowed the synthesis of several hydroxy-ketones (acyloins) with great structural diversity and in good overall yields. These acyloins in turn were easily transformed into 1,2-anti aminoalcohols through a highly diastereoselective reductive amination step. The synthetic utility of these approaches was exemplified by performing the syntheses of (±)-bupropion, a drug used to treat the abstinence syndrome of smoker and (±)-spisulosine, a potent anti-tumoral compound originally isolated form a marine source.
