Diastereoselective alkynylation of N-p-tolylsulfinylimines with aluminum acetylides.
The addition of alkynyl dimethyl aluminum compounds onto N-p-tolylsulfinylimines was investigated. The reaction was proved to be totally regioselective, leading to propargylamines with high diastereoselectivity (up to 99% de). Addition of aluminum derivatives gave a reversal of diastereoselectivity compared to the addition reaction of lithium acetylide.
Turcaud
Serge
S
Synthèse et Structure de Molécules d'Intérêt Pharmacologique, UMR 8638 CNRS, Université Paris-Descartes, Faculty of Pharmacy, 4 avenue de l'Observatoire, 75270 Paris cedex 6, France.
Berhal
Farouk
F
Royer
Jacques
J
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D000535:Aluminum / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011437:Propylamines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
D000480:Alkynes; D007097:Imines; D009942:Organometallic Compounds; D011437:Propylamines; D013454:Sulfoxides; C009054:propargylamine; D008094:Lithium; D010293:Pargyline; D000535:Aluminum