23085-60-1Relevant academic research and scientific papers
Base-promoted diastereoselective α-alkylation of borane: N -((S)-1′-phenylethyl)azetidine-2-carboxylic acid ester complexes
Tayama, Eiji,Nishio, Ryotaro,Kobayashi, Yoshiaki
supporting information, p. 5833 - 5845 (2018/08/22)
The base-promoted α-alkylation of N-((S)-1-phenylethyl)azetidine-2-carboxylic acid esters 1 was investigated. The use of diastereomerically pure borane complexes 3 as substrates, which are easily prepared from 1, dramatically improved the yields and diastereoselectivities of α-alkylated products 2. For example, the treatment of tert-butyl ester (1S,2S,1′S)-3a with 2.4 equivalents of lithium bis(trimethysilyl)amide (LiHMDS) at 0 °C followed by 2.6 equivalents of benzyl bromide afforded α-benzylated (2S,1′S)-2aa in 90% yield as almost a single diastereomer. Our method enables the production of optically active α-substituted azetidine-2-carboxylic acid esters starting from commercially available (S)-1-phenylethylamine, which is one of the least expensive chiral compounds.
Synthesis of Substituted Cyclopropanecarboxylates via Room Temperature Palladium-Catalyzed α-Arylation of Reformatsky Reagents
Greszler, Stephen N.,Halvorsen, Geoff T.,Voight, Eric A.
supporting information, p. 2490 - 2493 (2017/05/24)
The room temperature palladium-catalyzed cross-coupling of aromatic and heteroaromatic halides with Reformatsky reagents derived from 1-bromocyclopropanecarboxylates provides an exceptionally mild method for enolate α-arylation. The method is tolerant of a wide range of functionalities and dramatically shortens many of the existing routes to access widely used 1,1-disubstituted cyclopropanecarboxylate derivatives.
3-Pyridyl enantiomers and their use as analgesics
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, (2008/06/13)
The present invention relates to a method of controlling pain in mammals, including humans, comprising administering to a mammal or patient in need of treatment thereof selected compounds of formula I: STR1 or a pharmaceutically acceptable salt thereof. The invention further relates to selected (R) and (S) compounds of formula I above which are useful as analgesics as well as neuronal cell death preventors and anti-inflammatories.
ASSESSMENT OF CONFORMATION OF THE TETRAPEPTIDES Boc(L-Pro)4-OBn, Boc-(L-Aze-L-Pro)2-Opcp and Boc--Opcp
Zand L.,Tsai, F.-H.,Overberger, C. G.
, p. 35 - 47 (2007/10/02)
We have investigated the problem of the onset of helicity and the influence of proximal amino acids on the helical conformation of prolin oligopeptides and polymers by incorporating the four membered ring amino acid, azetidine-2-carboxylic acid, into some
USE OF HEXAMETHYLPHOSPHORAMIDE (HMPA) IN THE ALKYLATION OF AROMATIC AMINES: SYNTHESIS OF AZETIDINES, PYRROLIDINES, PIPERIDINES AND HEXAHYDROAZEPINES
Juaristi, Eusebio,Madrigal, Domingo
, p. 629 - 636 (2007/10/02)
The direct alkylation of p-toluidine, as a model of aromatic amines, with 1,3-, 1,4-, 1,5- and 1,6-ditosylates, -dibromides or -dimesitylates in HMPA as solvent affords the corresponding cyclic amines.The convenience of this reaction and some observed lim
