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Carbocations or Cyclopropyl Gold Carbenes in Cyclizations of Enynes
Author(s) -
PérezGalán Patricia,
Martin Nolwenn J. A.,
Campaña Araceli G.,
Cárdenas Diego J.,
Echavarren Antonio M.
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000557
Subject(s) - carbocation , chemistry , medicinal chemistry
Theoretical and experimental studies on the gold(I)‐catalyzed formal [4+2] cycloaddition of dienynes are consistent with a mechanism that proceeds by means of cyclopropyl gold(I) carbenes instead of simple carbocations. This work shows that homoallylic stabilization is significant even for systems in which the tertiary carbocation is stabilized by two methyl groups.