Metrics
1 Record Views
Journal article
Vanadium-Catalyzed Synthesis of Geometrically Defined Acyclic Tri- and Tetrasubstituted Olefins from Propargyl Alcohols
ACS catalysis, Vol.9(2), pp.1584-1594
02/01/2019
Web of Science ID: WOS:000458707000083
Abstract
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.
Related links
Details
- Title
- Vanadium-Catalyzed Synthesis of Geometrically Defined Acyclic Tri- and Tetrasubstituted Olefins from Propargyl Alcohols
- Publication Details
- ACS catalysis, Vol.9(2), pp.1584-1594
- Resource Type
- Journal article
- Publisher
- American Chemical Society
- Number of pages
- 21
- Grant note
- Franklin Veatch Memorial Award
- Copyright
- © 2019 American Chemical Society
- Identifiers
- WOS:000458707000083; 99381709173906600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English