93684-30-1

Upstream product

• 93684-54-9 4,5-dihydro-4-(1-methylethyl)-2-(2-phenylethyl)-3-(2-propenyl)oxazolinium 4-methylbenzenesulfonate 

Downstream Products

• 42361-59-1 (R)-2-phenylmethylpent-4-enoic acid 
• 93780-03-1 (S)-2-phenylmethylpent-4-enoic acid 
• 93684-65-2 (4S,1'S)-4-(1-Methylethyl)-2-(1-phenylmethyl-3-butenyl)-4,5-dihydrooxazole 
• 93684-37-8 (4S,1'R)-4-(1-Methylethyl)-2-(1-phenylmethyl-3-butenyl)-4,5-dihydrooxazole 
• 93780-05-3 (2R,1'S)-N-(1-(hydroxymethyl)-2-methylpropyl)-2-phenylmethyl-4-pentenamide 
• 93684-71-0 (2S,1'S)-N-(1-(hydroxymethyl)-2-methylpropyl)-2-phenylmethyl-4-pentenamide 

Relevant academic research and scientific papers

Asymmetric Induction in the Claisen Rearrangement of N-Allylketene N,O-Acetals

Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 1 is described.Diastereoselection noted for rearrangement 1->2 ranges from 84percent to 96percent and is a consequence of complete (Z)-N,O-acetal olefin selectivity in 1, high Cα-si-face selectivity in the rearrangement of 1 to 2, and the absence of Cα epimerization in oxazoline 2.Experiments which establish the steric bulk of the C4 appendage as a particularly important variable are also reported.Acid-catalyzed hydrolysis of rearranged oxazoline 2 completes an efficient, enantioselective synthesis of 2-substituted pent-4-enoic acid 4 and regenerates for recycling the chiral auxiliary reagent 3, initially prepared from inexpensive α-amino acids.