51799-48-5Relevant academic research and scientific papers
Reductive opening of 2-phenyl-1,3-dioxolanes by a naphthalene-catalysed lithiation: Synthetic applications
Gil, Juan F.,Ramon, Diego J.,Yus, Miguel
, p. 9535 - 9546 (2007/10/02)
The reaction of 2-phenyl-1,3-dioxolanes 1a,b with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in tetrahydrofuran at -40°C followed by successive reaction with an electrophile and final hydrolysis with water at the same temperature yields the corresponding monoprotected 1,2-diols 2aa-2bf. The same process but allowing to rise the temperature to 20°C before the hydrolysis affords alcohols 3aa-3bd. The use of 2,2-diphenyl-1,3-dioxolane 1d, under similar reaction conditions as for compounds 2, permits the isolation of 2,2-diphenylalcohols 11da-11dc, resulting from the reaction with two different electrophiles. A mechanistic rationalization for all processes is given.
New chiral auxiliaries: Their use in the asymmetric hydrogenation of β-acetamidocrotonates
Potin,Dumas,d'Angelo
, p. 3483 - 3486 (2007/10/02)
Synthesis of chiral β-amido esters 7 with high diasteroisomeric excess was achieved by asymmetric hydrogenation (H2/PtO2) of stereogenic β-acetamidocrotonates 6 in which the chirality is present in the alkyl of the ester part. For such a purpose, new efficient chiral auxiliaries such as 2,2-diphenylcyclopentanol (12) and 1,1-diphenyl-3-methyl-2-butanol (13) were developed.
