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Intramolecular Pd-catalyzed aryl-enone conjugate additions. Control of reductive vs non-reductive cyclization
Journal article   Peer reviewed

Intramolecular Pd-catalyzed aryl-enone conjugate additions. Control of reductive vs non-reductive cyclization

Gregory K Friestad and Bruce P Branchaud
Tetrahedron letters, Vol.36(39), pp.7047-7050
1995
DOI: 10.1016/0040-4039(95)01460-Y

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Abstract

Pd-catalyzed aryl-enone cyclization of 1 leads to Heck-type non-reductive cyclization product 3 and reductive cyclization product 4. Conditions have been developed to selectively form either 3 or 4 (or more highly functionalized 10 vs 11 or 13 vs 14). The formation of non-reductive cyclization products ( 3, 11, 14) requires an unusual apparent trans β-H elimination — some mechanistic possibilities that are consistent with the data are proposed.

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