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Beilstein J. Org. Chem. 2012, 8, 2202–2206, doi:10.3762/bjoc.8.248
Graphical Abstract
Scheme 1: Synthesis of tetrasubstituted olefins by a successive carbocupration and S–Li exchange.
Scheme 2: Proposed mechanism of the sulfur–lithium exchange starting with the alkenyl thioether 4.
Scheme 3: Synthesis of the precursor 1a.
Scheme 4: Carbocupration of the thioether 1a leading to the tetrasubstituted alkene 4a.
Scheme 5: Synthesis of the alkenyllithium reagent 7a by an S–Li exchange.
Scheme 6: Quenching of the alkynyllithium 7a. (Product ratios and diastereoselectivities were determined by 1...
Scheme 7: Synthesis and quenching of Z-styryllithium.