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Nickel-catalyzed reductive macrocyclization of ynals enables the selective synthesis of either endocyclic or exocyclic allylic alcohols from disubstituted alkynes by varying the ligand between phosphine and N-heterocyclic carbene. Novelty: ClaimNovelty.METHODOLOGICAL. Consensus alignment: ConsensusAlignment.NEUTRAL.

August 31, 2005

Access to Macrocyclic Endocyclic and Exocyclic Allylic Alcohols by Nickel-Catalyzed Reductive Cyclization of Ynals

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Abstract

Ni-catalyzed reductive macrocyclizations of ynals are reported. Disubstituted alkynes afford either endocyclic or exocyclic allylic alcohols depending on the ligand. Phosphine ligands favor the formation of endocyclic olefins, whereas N-heterocyclic carbene ligands favor the formation of exocyclic olefins. Terminal alkynes provide 1,2-disubstituted olefins with N-heterocyclic carbene ligands.

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