A convergent stereoselective synthesis of quinolizidines and indolizidines: chemoselective coupling of 2-hydroxymethyl-substituted allylic silanes with imines.
A convergent synthesis of stereodefined indolizidines and quinolizidines through chemoselective allyl transfer between 2-hydroxymethyl-substituted allylic silanes and imines is described. Overall, highly substituted heterocycles that contain three stereogenic centers and up to four fused rings can be accessed in two steps from relatively simple coupling partners.
Yang
Dexi
D
Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA.
Micalizio
Glenn C
GC
D007097:Imines / Q000737:chemistry*; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007097:Imines; D054836:Indolizidines; D020005:Propanols; D054837:Quinolizidines; D012821:Silanes; C006463:allyl alcohol