141192-61-2

Upstream product

• 1447173-45-6 C₂₀H₂₁NO₃ 
• 1575-74-2 (+-)-2-methyl-pent-4-enoic acid 
• 100-46-9 benzylamine 

Downstream Products

• 399031-53-9 (+/-)-hex-5-enoic acid benzyl(2'-methylpent-4'-enyl)amide 
• 399031-54-0 (+/-)-benzyl-9-methylazacyclodecan-2-one 
• 399031-55-1 (+/-)-1-benzyl-3-methylazacyclodecane 
• 201357-65-5 (+/-)-benzyl(2'-methylpent-4'-enyl)amine 
• 141192-47-4 2-Iodo-2-methyl-pent-4-enoic acid benzylamide 

Relevant academic research and scientific papers

Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu 3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals

2-Substituted amidyl radicals derived from 8a-d and 9a-d undergo acyl mode 5-exo-trig cyclisation to give 3,5-trans pyrrolidinones 11a-d and 14a-d as the major products in low diastereoselectivity (de = 9-36%). The steric nature of the nitrogen substituent attached to the amidyl radical does not have a significant effect on selectivity. The stereochemical outcome is opposite to that expected based upon applying the Beckwith rule.

Total synthesis of the putative structure of the marine alkaloid haliclorensin

Compound 1, the structure of which has been assigned to the marine natural product haliclorensin, was prepared by an unambiguous synthetic pathway and subjected to spectroscopic analysis. The derived data do not match those reported for the natural produc

Amino-Claisen rearrangements and Diels-Alder reactions of ketene N,O-acetals: Reactivity studies. On the way to a novel tandem process?

We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-substituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide 6 reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme g). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems rac-35-37 or to a β-lactam rac-34 were observed.