171019-33-3

Upstream product

• 33418-16-5 (-)-(R,Z)-1-(p-methylphenylsulfinyl)prop-1-ene 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 4801-58-5 N-hydroxypiperidine 
• 171019-27-5 (2S,3S,3aS)-2-Methyl-3-((R)-toluene-4-sulfinyl)-hexahydro-isoxazolo[2,3-a]pyridine 

Downstream Products

• 171019-34-4 (S)-2-[(1S,2S)-2-Hydroxy-1-((R)-toluene-4-sulfinyl)-propyl]-piperidine-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Asymmetric nitrone-vinyl sulfoxide cycloadditions

The cycloaddition of (Z) and (E)-vinyl sulfoxides with cyclic nitrones 1 and 2 is reported. Best diastereoselection is achieved with (Z)-vinyl sulfoxides 7a-d as dipolarophiles. This methodology allows the highly stereoselective synthesis of (+)-sedridine 9a, (-)-hygroline 10 and (-)-(2S)-N-carbomethoxypelletierine 11a.

Asymmetric Nitrone-Vinyl Sulfoxide Cycloadditions: a Highly Enantioselective Synthesis of (+)-Sedridine

Cycloaddition of 2,3,4,5-tetrahydropyridine-1-oxide 1 to (Z)-(R)-vinyl sulfoxides 2a-d proceeds in high yield to give isoxazolidines 3a-d and 4a-d with complete exo selectivity and with 82-98percent asymmetric induction.This method provides an efficient s