Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones.
ABSTRACT The hydrozirconation reaction of 1-alkynyl sulfoxides or sulfones with Cp2Zr(H)Cl in THF at room temperature predominantly gave Z-beta-zirconated vinyl sulfoxides or sulfones with excellent regioselectivity. Compared with 1-alkynyl sulfoxides, the hydrozirconation reaction of 1-alkynyl sulfones exhibits great synthetic potential, leading to the efficient preparation of Z-beta-halovinyl sulfones, Z-beta-sulfonyl alpha,beta-unsaturated ketones, and Z-beta-alkynyl vinyl sulfones. Although the reaction mechanisms are still not clear, the neighboring group participation of the sulfinyl or sulfonyl group may be playing an important role in this unique hydrozirconation reaction.
- SourceAvailable from: Stanislaw F Wnuk[Show abstract] [Hide abstract]
ABSTRACT: Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.Tetrahedron Letters 09/2009; 50(38):5424-5427. · 2.40 Impact Factor
- Angewandte Chemie International Edition 03/2010; 49(19):3338-41. · 11.34 Impact Factor
- [Show abstract] [Hide abstract]
ABSTRACT: A general method for the synthesis of α-substituted vinyl sulfones makes use of a combination of a triazole gold complex and gallium triflate. This efficient CS bond formation between simple terminal alkynes and sulfinic acids provides access to various α-substituted vinyl sulfones.Angewandte Chemie International Edition 04/2014; · 11.34 Impact Factor