ChemInform Abstract: Au(I)‐Catalyzed Cycloisomerizations Terminated by sp³ C—H Bond Insertion.

Abstract

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Gold-Catalyzed Synthesis of Small Rings

“…435 The group of Toste also described a sequential cycloisomerization/sp 3 192 (Scheme 48). 436,437 The observed inverse primary KIEs were tentatively explained by the formation of a σ complex between the hydrogen atom and the gold(I) center before the hydrogen transfer event.…”

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

“…The strategy employed relies on a sequence of gold-catalyzed cycloisomerization/ring expansion/Prins cyclization to produce the advanced tricylic compound 453 Two other examples of gold-catalyzed cycloisomerization reactions of 1,5-enynes substituted with a carbonyl functionality at the alkyne terminus were reported by the groups of Wang 181 and Toste (Scheme 103). 182 In the former case, cyclopropenyl carbinol 455 was shown to efficiently rearrange into phenol 456 in the presence of 1 mol % of a gold(I) complex at room temperature (Scheme 103, part A). An initial 5-endo-dig cyclization produces the bicyclohexene intermediate 457 which undergoes a ring fragmentation leading to the formation of gold carbenoid 458.…”