Asymmetric synthesis of alpha,alpha-dibranched propargylamines by acetylide additions to N-tert-butanesulfinyl ketimines.
Addition of lithium acetylides prepared from 1-pentyne, phenylacetylene, and trimethylsilylacetylene to diverse N-tert-butanesulfinyl ketimines affords a range of alpha,alpha-dibranched propargyl sulfinamides in generally good yields (up to 87%) and with high diastereoselectivities (up to >99:1). Acidic cleavage of the tert-butanesulfinyl group provides the free alpha,alpha-dibranched propargylamines.
Patterson
Andrew W
AW
Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720, USA.
Ellman
Jonathan A
JA
D002625:Chemistry, Organic / Q000379:methods*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011437:Propylamines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry
D011437:Propylamines; D013452:Sulfonium Compounds; C009054:propargylamine; D010293:Pargyline