118299-62-0

Upstream product

• 1374419-58-5 (E)-methyl 2-(1-benzylpyrrolidin-2-ylidene)acetate 
• 51804-12-7 Methyl 6-chloro-2-hexynoate 
• 100-46-9 benzylamine 
• 137256-28-1 4-(Benzyl-trimethylsilanylmethyl-amino)-butyraldehyde; hydrochloride 
• 477585-72-1 methyl (2S)-3-(1-benzylazetidin-2-yl)propanoate 
• 477585-71-0 methyl (2S)-3-(1-benzylazetidin-2-yl)prop-2E-enoate 
• 137256-46-3 methyl 6-amino>hex-2-enoate 

Relevant academic research and scientific papers

Total synthesis of indolizidine (+)-223A

We described the diastereoselective total synthesis of indolizidine (+)-223A in 10% overall yield over 14 steps starting from 6-chlorohex-2-ynoate. Our strategy involved chain elongation through aldolization, the formation of the indolizidine skeleton by cyclization, and stereocontrolled hydrogenation. We described the diastereoselective total synthesis of indolizidine (+)-223A in 10% overall yield over 14 steps starting from 6-chlorohex-2-ynoate. The influence of theN-protecting group of the starting pyrrolidine to form the indolizidine skeleton was studied. Copyright

Synthesis of chiral bicyclic azetidine derivatives

(2S)-N-Benzoyl-2-azetidinecarboxylic acid was converted into several derivatives of (5R)-1-azabicycloheptane via lactamization of 3-((2R)-azetidine)propanoic acid, subsequent aldol reaction and reduction. The structures of three stereoisomers of (5R)-3-(hydroxy-(4-nitrophenyl)methyl)-1-azabicyclo[3.2.0]heptan-2-one were determined by X-ray crystallography.

Oxidative methods for promoting iminium cation cyclization reactions

A new methodology for promoting iminium cation cyclization reactions, involving oxidation of α-silylamines, is presented.

Radical cyclization reactions of α-silyl amine α,β-unsaturated ketone and ester systems promoted by single electron transfer photosensitization

The results of a broad investigation of the preparative and mechanistic aspects of single electron transfer (SET) promoted photocyclization reactions of α-silyl amino and amido α,β-unsaturated esters and ketones are presented. A number of unique and synthetically useful features of these processes, driven by α-silyl amine and amide cation radical desilylation and by intramolecular conjugate addition of intermediate α-amino and α-amido carbon-centered radicals to unsaturated esters and ketones, are described. Comparisons of the SET-sensitized and direct irradiation promoted reactions of these systems have shown how the former method is superior in inducing photocyclization reactions in cases where the α,β-unsaturated ketone or ester excited states are too reactive to be quenched by SET from the tethered amine donors and where diradicals produced as intermediates in the direct-irradiation reactions undergo fragmentation rather than cyclization. The current efforts have also demonstrated that problems associated with the ready oxidation of intermediate α-amino radicals can be avoided by the proper selection of photosensitizer or amine N substituents. Lastly, the synthetic versatility of this chemistry, exemplified by its application to the preparation of a number of N-heterocyclic substances by pathways involving either exo or endo radical cyclization, is presented.