Asymmetric construction of quaternary centers by enantioselective allylation: application to the synthesis of the serotonin antagonist LY426965.
[reaction: see text] Catalytic enantioselective allylation with a chiral bisphosphoramide was applied to the synthesis of LY426965, a serotonin antagonist. The key step, addition of a 3,3-disubstituted allyltrichlorosilane to benzaldehyde, provided the adduct containing a stereogenic quaternary center with excellent diastereoselectivity and enantioselectivity.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Fu
Jiping
J
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D010880:Piperidines / Q000138:chemical synthesis*; D012702:Serotonin Antagonists / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D007202:Indicators and Reagents; D010880:Piperidines; D012702:Serotonin Antagonists; C458301:bicyclo(3.3.1)nonane; C412310:LY 426965