Asymmetric Synthesis of .BETA.-Hydroxy-.ALPHA.-amino Acid
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چکیده
منابع مشابه
Alpha Hydroxy Acid (AHA) / Beta Hydroxy Acid (BHA)
AHAs act on both the epidermal and the dermal levels. When applied to the skin, AHAs stimulate the exfoliation of epidermal cells in the stratum corneum (s.c.) by interfering with the ionic bonding between these cells. This results in the sloughing off dull, rough skin and promotes cellular renewal. Initially used for treatment of hyperkeratosis and other skin conditions affecting s.c. turnover...
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Addition of Potassium cyanide to a mixture of Schiff base and lithium perchlorate afforded a-aminonitriles in high yields. Addition of potassium cyanide to a methanolic solution of Schiff base and phosphoric acid afforded a-aminonitriles. When the reaction mixture was refluxed it gave a-amino acids in high yields.
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An enantioselective total synthesis of the natural amino acid (2S,4R,5R)-4,5-di-hydroxy-pipecolic acid starting from D-glucoheptono-1, 4-lactone is presented. The best sequence employed as a key step the intramolecular nucleophilic displacement by an amino function of a 6-O-p-toluene-sulphonyl derivative of a methyl D-arabino-hexonate and involved only 12 steps with an overall yield of 19%. The...
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[reaction: see text] One-pot asymmetric Mannich-hydrocyanation reactions are described. Reaction of unmodified aldehydes with N-PMP-protected alpha-imino ethyl glyoxylate in the presence of catalytic amounts of L-proline followed by the addition of Et(2)AlCN provided highly enantiomerically pure beta-cyanohydroxymethyl alpha-amino acid derivatives possessing three contiguous stereogenic centers...
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A direct asymmetric hydrogenation of unprotected enamino esters and amides is described. Catalyzed by Rh complexes with Josiphos-type chiral ligands, this method gives beta-amino esters and amides in high yield and high ee (93-97% ee). No acyl protection/deprotection is required.
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ژورنال
عنوان ژورنال: Journal of Synthetic Organic Chemistry, Japan
سال: 2005
ISSN: 0037-9980,1883-6526
DOI: 10.5059/yukigoseikyokaishi.63.1198