886-64-6Relevant articles and documents
Direct synthesis of phosphinopeptides containing C-terminal α-aminoalkylphosphinic acids
Meng, Fanhua,Xu, Jiaxi
experimental part, p. 533 - 538 (2010/11/04)
A series of phosphinopeptides containing C-terminal α- aminoalkylphosphinic acids were prepared in good yields directly in one-pot reactions of 2-(N-benzoxycarbonylamino)alkanamides/peptide amides, aldehydes, and aryldichlorophosphines, followed by hydrolysis. In the current method, the peptide bond was formed in a Mannichtype reaction. Springer-Verlag 2010.
EPC-synthesis of β-amino acid derivatives through lithiated hydropyrimidines
Seebach, Dieter,Boog, Alois,Schweizer, W. Bernd
, p. 335 - 360 (2007/10/03)
Racemic and enantiopure 2-tert-butyltetrahydropyrimidinones (from pivalaldehyde and 3-aminocarboxylic acids) are converted to Alloc-, Boc-, and Z-protected cyclic imino esters (7-10, Schemes 2-4). These are deprotonated to Li enaminates (K, L). Reactions with electrophiles (prim., sec. alkyl, allyl, benzyl, propargyl halides, aldehydes, imines, enoates) give good yields and are highly diastereoselective (products 11-42, Schemes 5-10). A two-step cleavage (removal of protecting group and hydrolysis) under very mild conditions converts the heterocyclic products to α-branched β-amino acid methyl esters (43-61, Schemes 11-13). The structure of the products is determined by NMR spectroscopy (Figure 1), by chemical correlation (Scheme 14), and by X-ray analysis (Figure 2, 3, 7, Table 1). A structure of the Li enaminates is proposed (Figure 4). Mechanistic models are derived for the reactions occurring with formation of two stereogenic centers with relative topicity like (Figures 5, 6).
THE REACTION OF BENZENE WITH N-(BENZYLOXYCARBONYL)-1-AMINOCYCLOPROPANE-1-CARBOXAMIDE
Tamura, Masahiro,Jacyno, John,Stammer, Charles H.
, p. 5435 - 5436 (2007/10/02)
The treatment of N-(benzyloxycarbonyl)-1-aminocyclopropane-1-carboxamide with benzene caused cleavage of the cyclopropane ring with the formation of a β-alaninamide derivative.
