Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
J Am Chem Soc. 2010 Jun 9;132(22):7576-7. doi: 10.1021/ja101513d.
The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. In the presence of P(SiMe(3))(3), this reductive coupling furnishes allyl boronic esters which are regioisomeric to those obtained with PCy(3) as the ligand. The coupling product may be subject to oxidation, which furnishes the derived 1,3-diol, or allylation with an additional aldehyde, which furnishes the derived 1,6-diol in a stereoselective fashion.
镍催化的羰基化合物和二烯的反应以区域和立体选择性的方式进行,使用当量的双(频哪醇)二硼。在 P(SiMe(3))(3)的存在下,这种还原偶联提供了烯丙基硼酸酯,其区域异构体与用 PCy(3)作为配体获得的那些相同。偶联产物可能会发生氧化,生成衍生的 1,3-二醇,或者与额外的醛进行烯丙基化,以立体选择性的方式生成衍生的 1,6-二醇。