This review describes the gold-catalyzed
reactions of specially
activated alkynes, allenes, and alkenes. Such species are characterized
by the presence of either electron-donating or electron-withdrawing
groups as substituents of the carbon π-system. They are intrinsically
polarized, and when compared to their nonspecially activated counterparts
can therefore be involved in gold-catalyzed transformations featuring
increased regio-, stereo-, and chemoselectivities. The chemistry of
specially activated carbon π-systems under homogeneous gold
catalysis is extremely rich and varied. The reactivity observed with
nonspecially activated unsaturated systems can often be transposed
to specially activated ones without loss of efficiency. However, specially
activated carbon π-systems also exhibit specific reactivities
that cannot be attained with regular substrates. In this family of
carbon π-systems, ynamides and their analogs, along with alkynyl
carbonyl derivatives, are the classes of substrates that have retained
the most attention. This review provides an overview of the chemistry
developed with all classes of specially activated carbon π-systems
by discussing their general and specific reactivities, presenting
and commenting on their gold-catalyzed transformations as well as
their applications.
The photochemical electrocyclization reaction of the title compound in the presence of β-cyclodextrin was examined in different conditions. No enantioselectivity was observed in solution, but solid-state reactions of a 1:1 complex as a suspension or a thin film, followed by reduction, provided (1R,5R)-2-azabicyclo[3.2.0]heptan-3-one in isolated yields up to 79% and with ee values up to 45%.
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