A convenient synthesis of chiral nonracemic vinyl aziridines
Organic Letters, 2004•ACS Publications
… In this paper, we disclose a convergent, flexible, and straightforward approach for the
synthesis of chiral nonracemic vinyl aziridines. Employing an approach developed by Hou
and Dai, 8 and recently extended within our laboratories, 9 reaction of allyl sulfur ylides with
chiral tert-butylsulfinylimines provides access to a series of nonracemic chiral vinyl
aziridines. Our previous work on the synthesis of chiral monosubstituted aziridines 10
exploited the high stereodirecting nature of the tert-butylsulfinyl group. Herein, we disclose …
synthesis of chiral nonracemic vinyl aziridines. Employing an approach developed by Hou
and Dai, 8 and recently extended within our laboratories, 9 reaction of allyl sulfur ylides with
chiral tert-butylsulfinylimines provides access to a series of nonracemic chiral vinyl
aziridines. Our previous work on the synthesis of chiral monosubstituted aziridines 10
exploited the high stereodirecting nature of the tert-butylsulfinyl group. Herein, we disclose …
The preparation of a range of alkyl and aryl chiral vinyl aziridines was achieved in high yield and stereoselectivity, and with excellent diastereoselectivity, by reaction of tert-butylsulfinylimines with the ylide derived from S-allyl tetrahydrothiophenium bromide.
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