Substituent-controlled reactivity in the Nazarov cyclisation of allenyl vinyl ketones
Alkyl substitution α to the ketone of an allenyl vinyl ketone enhances Nazarov reactivity by inhibiting alternative pathways involving the allene moiety and through electron donation and/or steric hindrance. This substitution pattern also accelerates Naza
Marx, Vanessa M.,Stoddard, Rhonda L.,Heverly-Coulson, Gavin S.,Burnell, D. Jean
Gold-catalyzed reactivity of 3-silyloxy-1,5-enynes: a synthetic tool for the synthesis of complex structures and its limitations
Gold-catalyzed reactions of 3-silyloxy-1,5-enynes in the presence of sterically demanding alcohols afford 4-acylcyclopentenes. The cascade process most likely proceeds through a 6-endo-dig carbocyclization and subsequent pinacol-type rearrangement. Studie
Stereocontrolled synthesis of heteroannular acetals from functionalized 1,5-enynes via radical cascades - Construction of quaternary and 1,2-diquaternary centres in polycyclic systems
Sequential, radical-mediated cyclizations of 1,5-enynes have been evaluated with respect to structure, stereochemistry and reactivity. In series A 5-exo-trig, 6-endo-dig cascades are favoured. The unusual 6-endo-dig cyclization is dictated by ring strain.
Rhode,Hoffmann
p. 6479 - 6488
(2007/10/03)
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