Organic Letters
Organic Letters
4 years ago

Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes

Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes
Liming Zhang, Xingguang Li, Xu Ma, Pei-nian Liu, Zhixun Wang
By using designed biphenyl-2-ylphosphines functionalized with a remote basic groups as ligands, N-alkynyl-o-nosylamides are directly converted to (1E,3E)-1-amido-1,3-dienes with excellent diastereoselectivities under gold catalysis. With allenamides as substrates, the gold-catalyzed isomerizations are high yielding and applicable to a broad substrate scope including various nitrogen protecting groups and exhibit unprecedented (3E)-selectivities for the distal C–C double bond and good regioselectivities. Combining this gold catalysis with one-pot Diels–Alder reactions leads to rapid assembly of valuable bicyclic compounds.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02624

DOI: 10.1021/acs.orglett.7b02624

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