147189-42-2Relevant academic research and scientific papers
Nickel/bis(oxazoline)-catalyzed asymmetric negishi arylations of racemic secondary benzylic electrophiles to generate enantioenriched 1,1-diarylalkanes
Do, Hien-Quang,Chandrashekar,Fu, Gregory C.
, p. 16288 - 16291 (2013/12/04)
A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft.
Synthesis of 4(S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone by SN2 cuprate displacement of an activated chiral benzylic alcohol
Quallich,Woodall
, p. 10239 - 10248 (2007/10/02)
Two routes for the preparation of 4(S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone are reported. The most efficient route generates a chiral benzylic alcohol by catalytic asymmetric oxazaborolidine reduction of a γ-ketoester that is subsequently activated and displaced in an SN2 manner with a higher order cuprate. Intramolecular Friedel-Crafts cyclization of the resulting t-butylester affords the title compound.
