361341-91-5

Upstream product

• 139190-64-0 Methyl (4S,E)-4--2-pentenoate 
• 151929-50-9 ethyl (2E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]pent-2-enoate 
• 120205-98-3 tert-butyl (N)-benzyl(1-oxopropan-2-yl)carbamate 
• 158380-71-3 tert-butyl (S)-benzyl(2-hydroxy-1-methylethyl)carbamate 
• 209266-07-9 methyl (S)-2-[(N-benzyl)-(N-t-butoxycarbonyl)amino]propanoate 

Downstream Products

• 361341-92-6 (E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate 
• 214632-83-4 3-benzyl-4-methyl-5-vinyloxazolidin-2-one 
• 361342-00-9 (4S,5S)-3-benzyl-4-methyl-5-vinyl-1,3-oxazolan-2-one 
• 361341-93-7 tert-butyl N-benzyl-N-[(1S,2E)-4-(isopropylsulfanyl)-1-methyl-2-butenyl]carbamate 
• 361341-94-8 N-(benzyl(4-toluenesulfonyl)-(2S,3E)-5-isopropylthio)pent-3-en-2-amine 
• 361341-96-0 isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate 
• 361341-97-1 isopropyl (3R)-3-((1S)-1-(benzyl((4-methylphenyl)sulfonyl)amino)ethyl)-2,2-dichloropent-4-enethioate 

Relevant academic research and scientific papers

Improved stereoselectivity in intramolecular SN2′ cyclization through use of mechanistic principles

Valine and alanine were converted into the corresponding α-hydroxy-β-amino acids through intramolecular SN2′ cyclization. The novel cyclization protocol relied upon the use of N-benzyl-protected carbamates derived from α-amino acids. Georg Thie

1,2-Asymmetric induction in the ketene Claisen rearrangement of (2S,3E)-5-(isopropylsulfanyl)-3-pentenes

The ketene Claisen rearrangement of chiral (2S,3E)-5-(isopropylsulfanyl)-3-penten-2-amines has been investigated by the semi-empirical AM1 method. The observed efficient direction of the 1,2-asymmetric induction in the ketene Claisen rearrangement has been modelled from comparison of the energies of the four possible transition states arising from two chair-like and two boat-like structures. The resulting trends of relative transition state energy are in reasonable agreement with experimental observations.