Tetrahedron Letters p. 7519 - 7522 (1995)
Update date:2022-07-31
Topics:
Gardiner, John M.
Giles, Philip, E.
Conjugate addition of thiophenol to γ-alkoxy-alkynone, 4, proceeds with up to 4:1 Z:E stereoselectivity.However, 2-mercaptobenzothiazole reacts to afford only the Z-isomeric vinyl sulfides.The Z-vinyl sulfides are readily converted to stereopure E-β-disubstituted enone, 8a, providing a convenient, practicable 2-step synthesis. 8a and 8b are also obtained via cuprate addition-equilibration, but with a Z:E ratio of View More
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