Silver-Assisted, Iridium-Catalyzed Allylation of Bis[(pinacolato)boryl]methane Allows the Synthesis of Enantioenriched Homoallylic Organoboronic Esters

• DOI: 10.1021/acscatal.6b00719
• Publication Date: 2016-04-22T14:40:53Z
• Authors: Miao Zhan; Ren-Zhe Li; Ze-Dong Mou; Chao-Guo Cao; Jie Liu; Yuan-Wei Chen; Dawen Niu
• Keywords: 01 natural sciences; 0104 chemical sciences; 3. Good health

Described 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.