1257323-87-7

Upstream product

• 106412-34-4 methyl 2-oxopiperidine-1-carboxylate 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 675-20-7 piperidin-2-one 

Downstream Products

• 1372716-09-0 methyl 6-((2-methoxyphenyl)(phenyl)phosphino)-3,4-dihydropyridine-1(2H)-carboxylate-borane complex 
• 1372716-15-8 1-(methoxycarbonyl)-6-((2S,5S)-1-oxo-2,5-diphenyl-λ5-phospholan-1-yl)-3,4-dihydro-2H-pyridine 
• 1372716-06-7 methyl 6-(diphenylphosphino)-3,4-dihydropyridine-1(2H)-carboxylate-borane complex 

Relevant academic research and scientific papers

Annulated N-Heterocycles by Tandem Gold(I)-Catalyzed [3,3]-Rearrangement/Nazarov Reaction of Propargylic Ester Derivatives: An Experimental and Computational Study

The gold(I)-catalyzed tandem rearrangement/Nazarov reaction of propargylic ester derivatives is a useful strategy for the synthesis of cyclopenta-fused N-heterocyclic structures present in many natural compounds. Readily available lactams are converted in

P-C cross-coupling onto enamides: Versatile synthesis of α-enamido phosphane derivatives

We report herein the Pd-catalyzed P-C cross-coupling reaction between enol phosphates and secondary phosphane-borane complexes or phosphane oxides. The reaction was performed under mild conditions, owing to Pd activation of the P-H bonds of the phosphane-

Enantiodivergent chemoenzymatic synthesis of 4-hydroxypiperidine alkaloids

An efficient chemoenzymatic synthesis of both enantiomers of fagomine, as well as of cis and trans-4-hydroxypipecolic acid is reported. The synthesis starts from commercial δ-valerolactam which, after a Pd-catalyzed methoxycarbonylation of the corresponding vinyl phosphate, is subjected to allylic oxidation to give a racemic 4-hydroxytetrahydropyridine derivative in 57% overall yield. This product is resolved by an enzyme-catalyzed esterification using immobilized lipases from Candida antarctica (Novozym 435) and Burkholderia cepacia (lipase PS Amano IM). The latter provides the corresponding R esters and the S alcohol in 95 and 94% ee, respectively. The S alcohol is then converted into L-fagomine by a stereoselective hydroboration/oxidation as key steps and the cis-(2R,4S)-4-hydroxypipecolic acid by stereoselective hydrogenation. The corresponding D-fagomine and cis-(2S,4R)-4-hydroxypipecolic acid, as well as trans-(2R,4R)-4-hydroxypipecolic acid can be prepared by the same strategy after hydrolysis of the R ester obtained by kinetic resolution. The lipase-catalyzed kinetic resolution of a racemic alcohol, readily obtained from commercial δ-valerolactam, is the key stepof an enantiodivergent synthesis of D- and L-fagomine as well as cis- and trans-4-hydroxypipecolic acid.