257296-71-2

Upstream product

• 298208-80-7 (E)-(S)-4-Amino-5-phenyl-pent-2-en-1-ol 
• 7722-84-1 dihydrogen peroxide 
• 280-64-8 9-bora-bicyclo[3.3.1]nonane 
• 208935-28-8 (4S-trans)-4,5-dihydro-4-benzyl-2-phenyl-5-vinyloxazoline 
• 257296-53-0 N-((2S)-5-acetoxy-1-phenyl-3-butenyl)benzamide 
• 303766-36-1 N-((E)-(S)-1-Benzyl-4-hydroxy-but-2-enyl)-benzamide 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 72155-45-4 Boc-L-phenylalaninal 
• 124818-94-6 ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 124818-93-5 (4S)-4-(N-tert-butoxycarbonyl)amino-5-phenyl-2-penten-1-ol 
• 35593-57-8 (S)-N-(1-oxo-3-phenylpropan-2-yl)benzamide 
• 5267-65-2 (S)-N-(1-hydroxy-3-phenylpropan-2-yl)benzamide 

Downstream Products

• 109389-15-3 N-(tert-Butyloxycarbonyl)-4(S)-amino-3(S)-hydroxy-5-phenylpentanol 
• 298208-76-1 (4S-trans)-4,5-dihydro-4-benzyl-2-phenyloxazoline-5-acetic Acid 
• 317322-37-5 1-((4S,5S)-4-benzyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-undecan-2-one 
• 317322-36-4 2-((4S,5S)-4-benzyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-acetamide 
• 210964-94-6 (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine 
• 125356-66-3 (+)-preussin 
• 885859-80-3 (3S,4S)-4-Amino-5-phenyl-pentane-1,3-diol 

Relevant academic research and scientific papers

Facile and efficient total synthesis of (+)-preussin.

[structure] The enantioselective total synthesis of (+)-preussin, a potent antifungal agent, has been achieved. The key steps are a Pd(0)-catalyzed oxazoline-forming reaction from L-phenylalanine, hydrogenolysis, and subsequent diastereoselective reductive cyclization of the intermediate aminoketone to pyrrolidine using Pearlman's catalyst.

Process for the preparation of oxazoline compound

The present invention relates to a process for the preparation of an oxazoline compound which is easily chemically converted to a beta-amino-alpha-hydroxy acid or a gamma-amino-beta-hydroxy acid. The method comprises producing a compound of the following formula (4) using alpha -amino acid. The produced compound (4) is subjected to an intramolecular cyclization to produce an oxazoline compound of the following formula (3). The oxazoline compound (3) is oxidized at a vinyl group with RuCl3 or NaIO4 to produce an oxazoline compound of the following formula (1) which is easily chemically converted to a beta-amino-alpha-hydroxy acid. Alternatively, the oxazoline compound (3) may also be treated with 9-borabiclo[3.3.1]nonane such that a hydroxy group is introduced into the end of the vinyl group of the oxazoline compound(3). The introduced end hydroxy group is oxidized with RuCl3 or NaIO4 to produce an oxazoline compound of the following formula (2) which is easily chemically converted to a gamma-amino-hydroxy acid.

Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0)

The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis and Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same π-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of β- amino-α-hydroxy acids 1 and γ-amino-β-hydroxy acids 2, conveniently protected as oxazoline.

Palladium-catalyzed formation and stereoselective isomerization of 5- vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3- hydroxy-5-phenylpentanoic acid

Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4- Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA).