5859-46-1Relevant academic research and scientific papers
1,3-asymmetric induction in stereoselective rhodium-catalyzed hydroformylation of homomethallylic alcohols
Breit, Bernhard
, p. 1123 - 1134 (1998)
Introducing ortho-diphenylphosphanyl benzoyl as a substrate bound catalyst directing group (CDG) allows an efficient substrate-directed diastereoselective hydroformylation of acyclic homomethallylic alcohols 5, making use of 1,3-asymmetric induction. The corresponding anti-aldehydes 10 were obtained as the major diastereomer in all cases, with diastereomer ratios of ca. 91:9 (anti-syn). Supporting evidence could be obtained for the ability of the o-DPPB group to act as a catalyst-directing group (CDG) via a reversible catalyst coordination. Finally, a model has been devised that rationalizes the origin of the 1,3-asymmetric induction. This model is based on a conformational analysis (NMR studies, MACROMODEL/MM3 calculations) of the homomethallylic substrates and indicates a relationship between the preferred substrate conformation and the experimentally determined stereoselectivities. In agreement with this model was the predicted significant improvement in stereoselectivity upon hydroformylation of the anti-homomethallylic alcohol derivative 15 (→ 21).
Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes
Kataoka, Yasutaka,Komori, Saki,Shimizu, Yuhei,Tanaka, Rina,Ura, Yasuyuki
supporting information, p. 570 - 574 (2022/02/02)
1,1-Disubstituted alkenes feature high steric hindrance, which renders their Wacker-type oxidation difficult. We demonstrate the stereoselective synthesis of 2-hydroxytetrahydrofurans via the Wacker-type oxidation of 3-methyl-3-buten-1-ols by using a PdCl
Accessing novel fluorinated heterocycles with the hypervalent fluoroiodane reagent by solution and mechanochemical synthesis
Browne, Duncan L.,Jones, Andrew C.,Riley, William,Singh, Kuldip,Stuart, Alison M.
supporting information, p. 7406 - 7409 (2021/08/03)
A new and efficient strategy for the rapid formation of novel fluorinated tetrahydropyridazines and dihydrooxazines has been developed by fluorocyclisation of β,γ-unsaturated hydrazones and oximes with the fluoroiodane reagent. Mechanochemical synthesis d
Formation of quaternary carbon centers by highly regioselective hydroformylation with catalytic amounts of a reversibly bound directing group
Ueki, Yusuke,Ito, Hideto,Usui, Ippei,Breit, Bernhard
supporting information; experimental part, p. 8555 - 8558 (2011/09/19)
Directly opposing Keulemans rule! Phosphinites work as reversibly bound directing groups allowing for the first highly regioselective hydroformylation of 3-substituted homoallylic alcohols to construct quaternary carbon centers. This method enables the at
