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
Abstract
Aziridination of vinylsilanes
PhCH![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
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.
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.
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