350237-04-6Relevant academic research and scientific papers
Asymmetric synthesis of acyclic 1,3-amino alcohols by reduction of N-sulfinyl β-amino ketones. Formal synthesis of (-)-pinidinol and (+)- epipinidinol
Davis, Franklin A.,Gaspari, Paul M.,Nolt, Brad M.,Xu, Peng
experimental part, p. 9619 - 9626 (2009/04/06)
(Chemical Equation Presented) Stereoselective reduction of acyclic N-sulfinyl β-amino ketones with (LiEt3BH) and Li(t-BuO) 3AlH, respectively, gave anti- and syn-1,3-amino alcohols with excellent selectivity. A formal asymmetric synthesis of the hydroxy piperidine alkaloids (-)-pinidinol and (+)-epipinidinol from a common N-sulfinyl β-amino ketone ketal precursor was developed. The pinidinol piperidine ring was formed via a novel acid-catalyzed cascade reaction of a N-sulfinylamino silyl protected alcohol ketal.
A diastereoselective intramolecular hydroamination approach to the syntheses of (+)-, (±)-, and (-)-pinidinol
Molander,Dowdy,Pack
, p. 4344 - 4347 (2007/10/03)
A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)2 converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100: 1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.
