Asymmetric synthesis of acyclic 1,3-amino alcohols by reduction of N-sulfinyl beta-amino ketones. Formal synthesis of (-)-pinidinol and (+)- epipinidinol.
Stereoselective reduction of acyclic N-sulfinyl beta-amino ketones with (LiEt(3)BH) and Li(t-BuO)(3)AlH, 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 beta-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.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19096, USA. fdavis@temple.edu
Gaspari
Paul M
PM
Nolt
Brad M
BM
Xu
Peng
P
D000605:Amino Alcohols / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000605:Amino Alcohols; D007202:Indicators and Reagents; D007659:Ketones; D010880:Piperidines; C431206:pinidinol