In 2017,Miura, Tomoya; Nakahashi, Junki; Murakami, Masahiro published 《Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid》.Angewandte Chemie, International Edition published the findings.Electric Literature of C13H26B2O4 The information in the text is summarized as follows:
(E)-δ-Boryl-substituted anti-homoallylic alcs. were synthesized in a highly diastereo- and enantioselective manner from 1,1-di(boryl)alk-3-enes and aldehydes. Mechanistically, the reaction consists of 1: Pd-catalyzed double-bond transposition of the 1,1-di(boryl)alk-3-enes to 1,1-di(boryl)alk-2-enes, 2: chiral phosphoric acid catalyzed allylation of aldehydes, and 3: Pd-catalyzed geometrical isomerization from the Z to E isomer. As a result, the configurations of two chiral centers and one double bond are all controlled with high selectivity in a single reaction vessel. In the experiment, the researchers used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Electric Literature of C13H26B2O4)
Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.Electric Literature of C13H26B2O4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts