1086509-64-9Relevant academic research and scientific papers
Synthesis of β-Amino Ketones by Addition of Aryl Methyl Ketones to Sulfinimines: Application to the Total Synthesis of HPA-12, Norsedamine, and Sedamine
Reddy, Arava Amaranadha,Prasad, Kavirayani R.
, p. 13488 - 13499 (2017)
Synthesis of β-sulfinamido ketones was accomplished by the addition of silyl enol ethers derived from arylmethyl ketones to chiral sulfinimines in excellent yield and selectivity. Application of the formed β-amino substituted ketones is exemplified in the total synthesis of sphingolipid HPA-12 and the sedamine alkaloids.
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.
