Journal
ACS CATALYSIS
Volume 9, Issue 2, Pages 1584-1594Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04567
Keywords
vanadium; tetrasubstituted olefins; alkenes; halogenation; vinyl halides; propargyl alcohols; Meyer-Schuster rearrangement
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Funding
- Franklin Veatch Memorial Award
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A highly selective formation of geometrically defined acyclic tri- and tetrasubstituted alkenes from inexpensive and readily available propargyl alcohols is described. Through vanadium oxo catalysis, tri- and tetrasubstituted alpha-chloro-, bromo-, and iodo-enone olefins can be synthesized with the kinetic E-geometry. Complementary tetrasubstituted bromo-, and iodo-enone olefins with Z-geometry can be accessed through a metal free 1,2-aryl shift. The utility of these geometrically defined vinyl halides is demonstrated through cross-coupling reactions to form all-carbon tetrasubstituted olefins with near complete retention of starting olefin geometry as well as through the total synthesis of (+/-)-myodesmone.
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