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. 2005 Sep 28;127(38):13156-7.
doi: 10.1021/ja054590i.

Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals

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Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals

Beth Knapp-Reed et al. J Am Chem Soc. .

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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