86087-22-1Relevant academic research and scientific papers
Expanding the scope of donor/acceptor carbenes to N -phthalimido donor groups: Diastereoselective synthesis of 1-cyclopropane α-amino acids
Alford, Joshua S.,Davies, Huw M. L.
, p. 6020 - 6023 (2013/02/23)
Warming of 4-phthalimido-N-mesyl-1,2,3-triazole in the presence of alkenes followed by silica gel induced hydrolysis results in a highly diastereoselective and catalyst-free entry to N-phthalimidocyclopropanecarboxaldehydes.
Stereoselective synthesis of 1-aminocyclopropanecarboxylic acid derivatives via ylide cyclopropanation of dehydroamino acid derivatives
Zhou, Rui,Deng, Xianming,Zheng, Juncheng,Shen, Qi,Sun, Xiuli,Tang, Yong
scheme or table, p. 995 - 1000 (2012/01/03)
1-Aminocyclopropanecarboxylic acid derivatives are synthesized from readily available dehydroamino acid derivatives via sulfur ylide. A range of different ylides are employed and the corresponding aminocyclopropanes are afforded with reasonable diastereoselection in good yields.
Diastereoselective Synthesis of Cyclopropane Amino Acids Using Diazo Compounds Generated in Situ
Adams, Luke A.,Aggarwal, Varinder K.,Bonnert, Roger V.,Bressel, Bettina,Cox, Russell J.,Shepherd, Jon,De Vicente, Javier,Walter, Magnus,Whittingham, William G.,Winn, Caroline L.
, p. 9433 - 9440 (2007/10/03)
A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ fro
Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid
Davies, Huw M. L.,Bruzinski, Paul R.,Lake, Debra H.,Kong, Norman,Fall, Michael J.
, p. 6897 - 6907 (2007/10/03)
The rhodium N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes leads to a very general method for the synthesis of functionalized cyclopropanes in a highly diastereoselective and enantioselective mode. A det
SYNTHESIS OF E AND Z 1-AMINO-2-ARYL(ALKYL)-CYCLOPROPANECARBOXYLIC ACID via MELDRUM DERIVATIVES
Izquierdo, M. L.,Arenal, I.,Bernabe, M.,Alvarez, E. Fernandez
, p. 215 - 220 (2007/10/02)
The reaction of 5-arylidene(alkylidene)-2,2-dimethyl-1,3-dioxane-4,6-diones (1) (Meldrum's acid derivatives) with dimethylsulfoxonium methylide gave 1-aryl(alkyl)-6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro octanes (2) which , on treatment with sodium meth
Reaction of 4-Methylene-5(4H)-oxazolones With Diazomethane
Arenal, I.,Bernabe, M.,Alvarez, E. Fernandez,Izquierdo, M. L.,Penades, S.
, p. 607 - 614 (2007/10/02)
The reaction of diazomethane with some (E) and (Z)-2-substituted-4-methylene-5(4)-oxazolones (1a-c) under two different conditions, has been studied. (E) and (Z)-1,2-disubstituted-7-oxo-6-oxa-4-azaspiro-hept-4-enes (3a-c, 4a-c) were mainly obtained, together with multiple addition compounds.The reaction showed to be stereoselective only when the substituents were aromatic.Acid hydrolysis of compounds 3a and 4a produced a mixture of (E) and (Z)-3,5-disubstituted-tetrahydrofuran-2-ones (8a, 9a).Smooth methanolysis of the ring led to (E) and (Z)-1-benzamido-cyclopropanecarboxylic esters (10a-c, 11a-c), which, on acid hydrolysis, gave (E) and (Z)-1-amino-2-phenylcyclopropanecarboxylic acids 12a and 13a.The pmr spectra have been analyzed by an iterative computer method, and the computed best values obtained have been used to deduce the stereochemistry of the spiroderivatives.
