ãFormation of Cyclopropanes via Activation of (γ-Methoxy)alkyl Gold(I) Complexes with Lewis Acidsã?was written by Kim, Nana; Widenhoefer, Ross A.. Recommanded Product: Bis[(pinacolato)boryl]methane And the article was included in Organometallics in 2020. The article conveys some information:
Treatment of the gold 3-methoxy-3-phenylpropyl complex (P)AuCH2CH2CH(OMe)Ph [P = P(t-Bu)2o-biphenyl] with AlCl3 at -78° led to the immediate (â? min) formation of a 4:1 mixture of phenylcyclopropane and (1-methoxypropyl)benzene in 86 ± 5% combined yield. Lewis acid activation of the stereochem. pure isotopomer erythro-(P)AuCH2CHDCH(OMe)Ph led to the formation of cis-2-deuterio-1-phenylcyclopropane in 84 ± 5% yield as a single stereoisomer, which established that cyclopropanation occurred with inversion of the γ-stereocenter. Similarly, ionization of the stereochem. pure cyclohexyl gold complex cis-(P)AuCHCH2CH(OMe)CH2CH2CH2 at -78° formed bicyclo[3.1.0]hexane in 82% ± 5% yield, which validated a low energy pathway for cyclopropanation involving inversion of the α-stereocenter. Taken together, these observations are consistent with a mechanism for cyclopropane formation involving backside displacement of both the γ-C leaving group and the α-C (L)Au+ fragment via a W-shaped transition state.Bis[(pinacolato)boryl]methane(cas: 78782-17-9Recommanded Product: Bis[(pinacolato)boryl]methane) was used in this study.
Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Recommanded Product: Bis[(pinacolato)boryl]methane Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts