110449-46-2

Upstream product

• 110449-37-1 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> <(2S)-2-(N,N'-di-tert-butoxycarbonyl)>hydrazinopropionate 
• 104897-88-3 N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((Z)-1-trimethylsilanyloxy-propenyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide 
• 104897-88-3 N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((E)-1-trimethylsilanyloxy-propenyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide 
• 96864-31-2 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl>propionate 

Downstream Products

• 6003-05-0 L-alanine hydrochloride 
• 119751-27-8 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> <(2R)-2-(N,N'-di-tert-butoxycarbonyl)>hydrazinopropionate 
• 104897-91-8 N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((Z)-4-methyl-1-trimethylsilanyloxy-pent-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide 
• 104926-26-3 <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate 
• 3082-75-5 L-Alanine ethyl ester 
• 96303-88-7 (-)-10-dicyclohexylsulfamoyl-D-isoborneol 

Relevant academic research and scientific papers

ENANTIOSELECTIVE SYNTHESES OF α-AMINO ACIDS FROM 10-SULFONAMIDO-ISOBORNYL ESTERS AND DI-t-BUTYL AZODICARBOXYLATE

Successive treatment of chiral esters 7 with LDA/Me3SiCl and di-t-butyl azodicarboxylate/TiCl4 and Ti(OiPr)4 gave N,N-di-t-butoxycarbonylhydrazinoesters 11 which on deacylation, hydrogenolysis, transesterification and acidic hydrolysis furnished (2S)-α-amino acid hydrochlorides 13 in good overall yields, high enantiomeric purity and with efficient recovery of the alcohol auxiliary 4.Experimental evidence for the configuration and conformation of the intermediate O-silyl ketene acetals 1 is provided.

Enantioselective Synthesis of α-Amino Acids from 10-(Aminosulfonyl)-2-bornyl Esters and Di(tert-butyl) Azodicarboxylate

Successive treatment of chiral esters 1 with LiN(i-Pr)2/Me3SiCl and di(tert-butyl) azodicarboxylate/TiCl4/Ti(i-PrO)4 gave N,N'-dihydrazino esters 9 which on deacylation, hydrogenolysis, transesterification, and acidic hydrolysis furnished (2S)-α-amino acids 6 in high enantiomeric purity with efficient recovery of the auxiliary alcohol 7.