445018-41-7

Upstream product

• 309757-65-1 (3R,αS)-tert-Butyl 3-(N-α-methyl-4-methoxybenzylamino)-3-phenyl propanoate 
• 6298-96-0 1(R)-(4-methoxyphenyl)-ethylamine 
• 100-52-7 benzaldehyde 
• 120343-46-6 (S)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine 
• 309757-64-0 (3R,αS)-tert-Butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-phenyl propanoate 
• 160460-40-2 [(S)-1-(4-Methoxy-phenyl)-ethyl]-[1-phenyl-meth-(E)-ylidene]-amine 
• 6298-96-0 (S)-1-(4-methoxyphenyl)ethylamine 
• 14990-09-1 tert-butyl cinnamate 

Downstream Products

• 445018-42-8 (4R,αS)-N-(α-methyl-4-methoxybenzy)-4-phenylazetidin-2-one 
• 37088-65-6 (3R)-4-phenyl-2-azetidinone 

Relevant academic research and scientific papers

Synthetic versatility of 2-substituted-6-methyl 2,3-dihydropyridinones in the synthesis of polyfunctional piperidine-based compounds and related β amino acid derivatives

Chiral 2-substituted-6-methyl 2,3-dihydropyidinones 9, which can be facilely obtained from an asymmetric vinylogous Mannich reaction (VMR) with 1,3-bis-trimethysily enol ether, were used as versatile intermediates in constructing chiral polyfunctional piperidine-based compounds. The 6-methyl group of such compounds can be conveniently functionalized via alkylation and acylation reactions to provide efficient entries to the synthesis of a variety of chiral multi-substituted piperidine-based compounds. Further elaboration of the corresponding intermediates also provided access to polyfunctional indolizidine-based compounds. These methods were showcased in an asymmetric synthesis of 2,6-di-substituted piperidine compound 13, reported as the key intermediate in the synthesis of (+)-calvine and a natural alkaloid (-)-indolizidine 209D. Furthermore, selective C5 iodination of compound 9 enabled the installation of additional functional groups at this position. Finally, we demonstrated that the oxidative cleavage of 2-substituted-6-methyl-2,3-dihydropyidinones is a practical and efficient method for the enantioselective synthesis of β-amino acids, which can undergo further intra-molecular cyclization to give the corresponding chiral four-membered β-lactam derivatives.

Orthogonal N,N-deprotection strategies of β-amino esters

β-Amino esters derived from the stereoselective conjugate addition of homochiral lithium N-benzyl-N-α-methyl-4-methoxybenzylamide to α,β-unsaturated esters may be orthogonally mono-N-deprotected under either oxidative or acid-promoted reaction conditions. Further oxidative deprotection affordsβ-amino acids or β-lactams.