920512-69-2Relevant academic research and scientific papers
Stereodivergent diversity oriented synthesis of piperidine alkaloids
Adriaenssens, Louis V.,Austin, Carolyn A.,Gibson, Mairi,Smith, David,Hartley, Richard C.
, p. 4998 - 5001 (2007/10/03)
Alkylidenetitanium reagents enable the reagent-controlled high throughput asymmetric synthesis of 2-substituted piperidines and rapid access to multiple cyclic imines using solid phase synthesis (SPS). The Schrock carbenes, generated by reduction of thioacetals, convert resin-bound esters into enol ethers. Treatment with acid releases amino ketones that are cyclized with TMSCl to give iminium salts. Reduction introduces a chiral centre at C-2, whose absolute stereochemistry is determined by a phenethylamine (PEA) chiral auxiliary. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
