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Unprecedented Reversal of Regioselectivity during Methanolysis and an Interception of Curtius Rearrangement
Author(s) -
Mandal Mihirbaran,
Buevich Alexei V.,
Wang Hongwu,
Brunskill Andrew,
Orth Peter,
Caldwell John P.,
Liu Xiaoxiang,
Mazzola Robert,
Cumming Jared,
McKittrick Brian,
Zhu Zhaoning,
Stamford Andrew
Publication year - 2021
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.202101056
Subject(s) - regioselectivity , chemistry , curtius rearrangement , nitrene , moiety , stereochemistry , organic chemistry , combinatorial chemistry , catalysis
Unprecedented reversal in regioselectivity during methanolysis of anhydrides due to the change in substitution pattern of fluorine in the phenyl moiety, and the formation of nitrene intercepted intermediates during Curtius rearrangement of the acids were the major impediments for discovering bioactive molecules in beta amyloid cleaving enzyme‐1 (BACE1) program. Solutions to these synthetic challenges, and our investigation into this unexpected change in reactivity are discussed.