88264-44-2Relevant academic research and scientific papers
A three-step route to a tricyclic steroid precursor
Taber, Douglass F.,Sheth, Ritesh B.
, p. 8030 - 8032 (2008/12/22)
(Chemical Equation Presented) 2-Alkyl cyclohexenones are useful intermediates for organic synthesis. The Wittig reaction of a series of aldehydes with (cyclopropylmethyl)triphenylphosphonium bromide delivered the corresponding alkenyl cyclopropanes. UV irradiation in the presence of Fe(CO)s converted the alkenyl cyclopropanes to the 2-substituted cyclohexenones. This approach enabled a three-step synthesis of the tricyclic core of estrone methyl ether.
Regioselective Lewis Acid-mediated α-tert-Alkylation of Acyloins and Glycolic Acid
Reetz, Manfred T.,Heimbach, Horst
, p. 3702 - 3707 (2007/10/02)
O,O'-Bis-silylated acyloins 10a-h as well as the tris-silylated form 13 of glycolic acid (7) can be tert-alkylated with tert-butyl chloride or 1-adamantyl bromide in the presence of catalytic amounts of ZnCl2.In case of unsymmetrically substituted derivatives, complete regioselectivity according to the Markovnikov rule is observed.The adamantylated acyloins are converted into α,β-unsaturated α-adamantyl ketones 27-30 upon treatment with H2SO4.
