The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane( cas:97739-46-3 ) is researched.Category: tetrahydropyran.Clarke, Matthew L.; Roff, Geoffrey J. published the article 《Highly regioselective rhodium-catalyzed hydroformylation of unsaturated esters: The first practical method for quaternary selective carbonylation》 about this compound( cas:97739-46-3 ) in Chemistry – A European Journal. Keywords: regioselective hydroformylation unsaturated carboxylic acid ester rhodium phosphine catalyst; alkyne conversion amino acid ester. Let’s learn more about this compound (cas:97739-46-3).
Highly regioselective hydroformylation of unsaturated esters can be achieved when a highly reactive, ligand-modified, rhodium catalyst is employed near ambient temperatures (15-50°C) and pressures over 30 bar. The use of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane shows distinct advantages over other commonly applied phosphanes in terms of reaction rate, and regio- and chemoselectivity. Hydroformylation of a range 1,1-di-, and 1,1,2-trisubstituted unsaturated esters yields quaternary aldehydes that are forbidden products according to Keulemans Rule. The aldehydes can be reductively aminated with mol. hydrogen to give β-amino acid esters in high yield. The overall green chem. process involves converting terminal alkynes into unusual β-amino acid esters with only water generated as an essential byproduct. This catalytic system has also been applied to the hydroformylation of simple 1,2-disubstituted unsaturated esters, which were hydroformylated with excellent α-selectivity and good chemoselectivity.
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics