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N ‐Amino‐ exo ‐3,6‐epoxy‐1,2,3,6‐tetrahydrophthalimide as an Active Aminoaziridinating Agent
Author(s) -
Zibinsky Mikhail,
Stewart Timothy,
Prakash G. K. Surya,
Kuznetsov Mikhail A.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900326
Subject(s) - chemistry , epoxy , alkyl , aryl , medicinal chemistry , organic chemistry , stereochemistry
Abstract N ‐Amino‐ exo ‐3,6‐epoxy‐1,2,3,6‐tetrahydrophthalimide is active in the oxidative aminoaziridination reaction toward alkenes substituted with aryl‐, alkyl, and electron‐withdrawing groups, providing access to stable derivatives of N ‐aminoaziridine. Yields varied from 19 to 76 %, and trans ‐substituted alkenes reacted faster and gave better yields than cis ‐alkenes. No products of self‐aziridination were isolated.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)