cs6b00719_si_001.pdf (12.85 MB)
Silver-Assisted, Iridium-Catalyzed Allylation of Bis[(pinacolato)boryl]methane Allows the Synthesis of Enantioenriched Homoallylic Organoboronic Esters
journal contribution
posted on 2016-04-22, 00:00 authored by Miao Zhan, Ren-Zhe Li, Ze-Dong Mou, Chao-Guo Cao, Jie Liu, Yuan-Wei Chen, Dawen NiuDescribed here is
an enantioselective approach of making chiral,
β-substituted homoallylic organoboronic esters. In the presence
of LiOtBu and a catalytic amount of silver
salt, commercial bis[(pinacolato)boryl]methane participated in the
iridium-catalyzed asymmetric allylation reactions, delivered a “CH2B(pin)” group, and yielded the title compounds from
allylic carbonates. The synthetic utility of the prepared chiral organoboronates
was demonstrated by their conversion to other important classes of
compounds.