Highly diastereoselective zinc-catalyzed propargylation of tert-butanesulfinyl imines.
A zinc-catalyzed diastereoselective propargylation of t-butanesulfinyl imines is presented. The methodology provided both aliphatic and aryl homopropargylic amines in up to 98:2 and 99.8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthesis of a cis-substituted pyrido-indole through a diastereoselective Pictet-Spengler cyclization.
Fandrick
Daniel R
DR
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. daniel.fandrick@boehringer-ingelheim.com
Johnson
Courtney S
CS
Fandrick
Keith R
KR
Reeves
Jonathan T
JT
Tan
Zhulin
Z
Lee
Heewon
H
Song
Jinhua J
JJ
Yee
Nathan K
NK
Senanayake
Chris H
CH
D000480:Alkynes; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D000480:Alkynes; D000588:Amines; D006576:Heterocyclic Compounds, 4 or More Rings; D007097:Imines; D020005:Propanols; D013452:Sulfonium Compounds; C028255:propargyl alcohol; D015032:Zinc