177018-15-4Relevant articles and documents
Desilylative elimination of the quinazolinone ring from 1-(4-oxoquinazolin-3-yl)-2-silylaziridines; preparation of an N-H aziridine in high enantiomeric excess by in situ nucleophilic addition to the derived azirine
Atkinson, Robert S.,Coogan, Michael P.,Lochrie, Ian S. T.
, p. 897 - 900 (2007/10/03)
Aziridination of vinylsilanes PhCH=CHSiR3 (R = Me, Et, Ph) with enantiopure 3-acetoxyaminoquinazolinone 11 gives the corresponding aziridines 12 [diastereoisomer ratio (dr) 10:1], 18 (dr 13:1) and 20 (dr 2:1). Desilylative elimination of the quinazolinone from these aziridines by caesium fluoride in the presence of cyanide gives aziridine 14 by cyanide addition to the 3-unsubstituted azirine 13, produced in situ. Acylation of aziridine 14 with (S)-acetoxypropionyl chloride gives N-acylaziridine 16; the good correlation between the diastereoisomer ratios of aziridines 12, 18 and 20 and those of the N-acylaziridine 16 produced in each case suggests that intermediate azirine 13 is configurationally stable.
Preparation of N-H aziridines in high enantiomeric excess by in situ aziridine-azirine-aziridine interconversion
Atkinson, Robert S.,Coogan, Michael P.,Lochrie, Ian S. T.
, p. 789 - 790 (2007/10/03)
Aziridine 6 is produced highly diastereoselectively by treatment of enantiopure 3-acetoxyaminoquinazolinone 4 (Q*NHOAc) with β-trimethylsilylstyrene: desilylative elimination of Q* and in situ addition of cyanide to the intermediate azirine gives the NH-a
