202926-03-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 202926-16-7 (R)-N-(1-phenylethyl)-5-hexenylamine 
• 17482-21-2 1-(hex-5-en-1-ylsulfonyl)-4-methylbenzene 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 1029019-96-2 tert-butyl N-(5-oxopentyl)-N-[(R)-(1-phenylethyl)]carbamate 
• 2740-00-3 indolizidin-3-one 
• 13618-93-4 indolizidine 
• 202926-05-4 [5-Iodo-6-(toluene-4-sulfonyl)-hexyl]-((R)-1-phenyl-ethyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Asymmetric aza-Michael addition: synthesis of (-)-allosedridine and (-)-2-epi-ethylnorlobelol

The combination of cross-metathesis and aza-Michael addition is an efficient method for generating piperidine alkaloids. Allosedridine and 2-epi-ethylnorlobelol were synthesized in six steps with ca. 25% overall yield. The aza-Michael addition is reversible for phenyl and alkyl ketones; however, the epimerization is not observed for the corresponding ester and amide.

Synthesis of 2-substituted nitrogen heterocycles using para-toluenesulfonyl iodide in a key step

N-Protected aminoalkenes undergo radical addition of tosyl iodide to give β-iodosulfones which can subsequently be induced to cyclise giving 2-substituted pyrrolidines and piperidines. Incorporation of an α-methylbenzyl group at nitrogen leads to a diastereoselective ring closure where the constituent diastereoisomers can be separated readily giving chiral, non-racemic heterocycles.