154499-08-8

Upstream product

• 87905-98-4 5-<(benzyloxycarbonyl)amino>pentanol 
• 188530-60-1 (5-oxo-pentyl)-carbamic acid benzyl ester 
• 1092462-13-9 (E)-benzyl 7-(benzoyloxy)oct-5-enylcarbamate 
• 154499-09-9 (E)-8-benzyloxycarbonylamino-3-octen-2-one 

Downstream Products

• 154499-15-7 Acetic acid (E)-(R)-7-benzyloxycarbonylamino-1-methyl-hept-2-enyl ester 
• 154499-17-9 C₁₈H₂₅NO₄ 

Relevant academic research and scientific papers

An efficient synthesis of 2- and 2,6-substituted piperidines using Pd II-catalyzed 1,3-chirality transfer reaction

(Chemical Equation Presented) An efficient and general method for 2- and 2,6-substituted piperidine syntheses using PdII-catalyzed 1,3-chirality transfer reaction has been developed. The various N-protected ζ-amino allylic alcohols cyclize in the presence of PdCl 2(CH3CN)2 to give substituted piperidines with high stereoselectivities. The syntheses of (S)-(+)- and (R)-(-)-coniine were achieved in 3 steps from the optically pure allylic alcohols (S)-14c and (R)-14c, respectively. Although the rates of reactions were significantly accelerated in CH2Cl2, THF gave the highest stereoselectivity. PdCl2(CH3CN)2 was found to be the best catalyst for this transformation. A plausible reaction pathway involving the formation of the Pd π-complex directed by the chiral secondary allylic alcohol followed by syn-azapalladation, and subsequent syn-elimination of PdCl(OH) is proposed.

Construction of Chiral 2-functionalized Piperidine via Enzymatic Resolution and Palladium-catalyzed N-Alkylation

The palladium-catalyzed cyclization of the optically active urethan , which was obtained by enzymatic resolution of the racemic alcohol (1), gave the piperidine 6.This reaction affords highly efficient intramolecular chirality transfer.Compound 6 was converted into (+)-coniine and 2-hydroxymethylpiperidine.