S-Cyanosilylenolethers: Preparation and Potential Intermediates in Synthesis
- 1 January 1978
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 8 (4) , 231-239
- https://doi.org/10.1080/00397917808065614
Abstract
In a previous paper we reported the direct α-phenylsulfenylation of enolates generated during different 1,4-addition reactions on α,β-unsaturated ketones1. Since Nagata has shown that the conjugate addition of a cyano group with diethylaluminum cyanide leads to an aluminum enolate2,3, it would be worthwile to investigate the potentiality of this reagent for simultaneous functionalisation at the α-position. Initial experiments for in situ trapping with phenylsulfenylchloride gave disappointing low yields (< 15%). However working up the initially formed aluminumenolate with trimethylchlorosilane and pyridine afforded the corresponding silylenolethers in very good yields4 (Table I).Keywords
This publication has 7 references indexed in Scilit:
- Note on the Direct α‐Phenylsulfenylation of Enolates Generated During 1, 4‐Addition Reactions on α, β‐Unsaturated KetonesBulletin des Sociétés Chimiques Belges, 1977
- O-Silylated Enolates - Versatile Intermediates for Organic SynthesisSynthesis, 1977
- Herstellung α‐thiolierter CarbonylverbindungenEuropean Journal of Inorganic Chemistry, 1976
- Quaternary ammonium enolates as synthetic intermediates. Regiospecific alkylation reaction of ketonesJournal of the American Chemical Society, 1975
- Hydrocyanation. VII. Stereochemistry of conjugate hydrocyanation of cyclic .alpha.,.beta.-unsaturated ketonesJournal of the American Chemical Society, 1972
- Hydrocyanation. IV. New hydrocyanation methods using hydrogen cyanide and an alkylaluminum, and an alkylaluminum cyanideJournal of the American Chemical Society, 1972
- Silyl alkenyl ethers as the synthetic equivalent of enols. New syntheses of β-keto-sulphides and 1,3-diketonesJournal of the Chemical Society, Chemical Communications, 1972