140135-91-7Relevant academic research and scientific papers
In situ formation of allyl ketones via Hiyama-Nozaki reactions followed by a chromium-mediated Oppenauer oxidation
Schrekker, Henri S.,De Bolster, Martin W. G.,Orru, Romano V. A.,Wessjohann, Ludger A.
, p. 1975 - 1981 (2002)
In Hiyama-Nozaki reactions of allylchromium with aldehydes the expected products are homo-allylalcohols. However, oxidation products derived from these, predominantly allyl ketones, can be common side products. This can be explained by an Oppenauer-(Meerwein-Ponndorf-Verley)-type mechanism (OMPV-reaction). The amount of oxidation is strongly dependent on the substitution pattern of the reaction partners and the reaction conditions. An appropriate choice of these can lead to preferential formation of ketones instead of the alcohols. In addition to its synthetic usefulness, the oxidation-reduction equilibrium is of the utmost importance for the design of enantioselective Hiyama-Nozaki reactions because it is also a potential racemization pathway.
Allylation of Aldehydes by Allyl- and Crotyltributyltin in the Presence zof Catalytic Amounts of Bu2SnCl2 Complex
Yano, Katsunori,Baba, Akio,Matsuda, Haruo
, p. 66 - 70 (2007/10/02)
In nearly neutral media, the reaction of allylic tributyltin with aldehydes is effectively catalyzed by Bu2SnCl2 complexes.The addition of coordinative reagents and benzoyl chloride as a quencher is required of the catalytic allylation, furnishing homoall
