79898-18-3

Upstream product

• 121-39-1 ethyl 3-phenylglycidate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 19190-78-4 potassium trans-3-phenyloxiranecarboxylate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1566-68-3 (2RS,3SR)-2,3-epoxy-3-phenyl-propionic acid 

Downstream Products

• 114376-13-5 (3S,4R,5R)-clausenamidone 
• 79898-17-2 (2S,3R)-β-phenylglycidic acid 
• 114528-76-6 (3S,4R,5R,6R)-epi-cis-clausenamide 
• 79869-89-9 N-<(2S,3S)-2-acetoxy-3-dimethylamino-3-phenylpropionyl>-(R)-α-methylbenzylamine 
• 79869-88-8 N-<(2S,3S)-3-dimethylamino-2-hydroxy-3-phenylpropionyl>-(R)-α-methylbenzylamine 
• 79898-21-8 N-<(2S,3R)-2,3-epoxy-3-phenylpropionyl>-(R)-α-methylbenzylamine 

Relevant academic research and scientific papers

The preparation of optically active epineoclausenamide and enantiomeric separation of its racemate

We synthesized the optically active epineoclausenamide by utilizing chiral reagents, such as R-α-methylbenzylamine and S-α-methylbenzylamine, for the resolution of the intermediate (trans-3-phenyl-oxiranecarboxylic acid 12), followed by amide exchange, cy

Efficient synthesis of (-)-clausenamide

A new method for the synthesis of (-)-clausenamide was reported. (-)-clausenamide was obtained from the inexpensive material of trans-cinnamic acid within five steps with overall yields of 8.9% and ee 99.5%. Compared with the multi-step asymmetric synthes

Synthesis of the spermidine alkaloids (-)-(2R,3R)- and (-)-(2R,3S)-3-hydroxycelacinnine: Macrocyclization with oxirane-ring opening and inversion via cyclic sulfamidates

The two epimers (-)-1a and (-)-1b of the macrocyclic lactama kaloid 3-hydroxycelacinnine with the (2R,3R) and (2R,3S) absolute configurations, respectively, were synthesized by an alternative route involving macrocyclization with the regio- and stereoselective oxirane-ring opening by the terminal amino group (Schemes 2 and 6). Properly N-protected chiral trans-oxirane precursors provided (2R,3R)-macrocycles after a one-pot deprotection-macrocyclization step under moderate dilution (0.005-0.01M). The best yields (65-85%) were achieved with trifluoroacetyl protection. Macrocyclization of the corresponding cis-oxiranes was unsuccessful for steric reasons. Inversion at OH-C(3) via nucleophilic displacement of the cyclic sulfamidate derivative with NaNO2 led to (2R,3S)-macrocycles. The synthesized (-)-(2R,3S)-3-hydroxycelacinnine ((-)-1b) was identical to the natural alkaloid.

ASYMMETRIC HYDROGENATION CATALYZED BY (ACHIRAL BASE)BIS(DIMETHYLGLYOXIMATO)COBALT(II)-CHIRAL COCATALYST SYSTEM.

Chiral tertiary amines with a secondary amide group at alpha - or beta -carbon were prepared, and an asymmetric hydrogenation of methyl 2-(acetylamino)acrylate and N,N prime -dimethyl-5-benzylidenehydantoin catalyzed by achiral base-coordinated bis(dimethylglyoximato)cobalt(II)-chiral cocatalyst system was examined by using each of them as the cocatalyst. The enantiomeric excess of N,N prime -dimethyl-5-benzylhydantoin reached 79. 1% with (S)-N- left bracket (R)-1-phenylethyl right bracket -2-quinuclidinecarboxamide as the cocatalyst. Remarkable differences were observed in the enantioselectivities between the two substrates for the same cocatalysts.