Stereoselective synthesis of trifluoromethylated vicinal ethylenediamines with alpha-amino N-tert-butanesulfinimines and TMSCF3.
Isolable alpha-amino N-tert-butanesulfinimines were prepared through the condensation of Reetz's alpha-amino aldehydes (prepared from alpha-amino acids) with Ellman's (R)-N-tert-butanesufinamide without any racemization, and these were trifluoromethylated with TMSCF3 and TMAF (tetramethylammonium fluoride) to the corresponding vicinal ethylenediamines derivatives. Imines derived from l-amino acids gave exclusively one diastereomer with a very high yield.
Prakash
G K Surya
GK
Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, California 90089-1661, USA. GPRAKASH@USC.EDU
Mandal
Mihirbaran
M
D005029:Ethylenediamines / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013452:Sulfonium Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D005029:Ethylenediamines; D006845:Hydrocarbons, Fluorinated; D012821:Silanes; D013452:Sulfonium Compounds; D014753:Vinyl Compounds; C509472:trimethyl(trifluoromethyl)silane