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- W2011003320 abstract "Hydroxyl-directed aziridination of the isoprenoid alcohols — geraniol, nerol, and(E,E)-farnesol— with Atkinson'sN-acetoxyamino-2-ethyl-4(3H)-quinazolonereagent (4) affordedN-substituted2,3-epimino alcohols. Reduction of these and relatedN-substitutedaziridines with metal-ammonia or lithium-naphthalenide reagents furnished a series of N-H aziridino alcohols (53–74%) including 2,3- and 6,7-epimino geraniols (10 and13), 2,3-epimino nerol (17),(E,E)-2,3-epiminofarnesol (23), andsyn-2,3-epimino isophorol (20). A less efficient synthesis of thetrans-2,3-epimino isoprenoid alcohols10 and23 by irradiation of allylic azidoformates and hydrolysis of the oxazolidinone photoproducts is also reported. These approaches complement known methods for synthesis of N-H aziridines of isoprenoid polyenes. Regioselective conversion of isoprenoid alcohols toN-Haziridino alcohols by aziridination withN-acetoxyamino-2-ethylquinazoloneand metal-ammonia reduction is described.Download : Download full-size image" @default.
- W2011003320 created "2016-06-24" @default.
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- W2011003320 date "1999-08-01" @default.
- W2011003320 modified "2023-10-17" @default.
- W2011003320 title "Regio- and stereoselective synthesis of N-H aziridines N-N bond reduction ofN-quinazolinylaziridines" @default.
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- W2011003320 doi "https://doi.org/10.1016/s0040-4020(99)00522-0" @default.
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