Acceleration effect of Lewis acid in allylboration of aldehydes: catalytic,regiospecific, diastereospecific,and enantioselective synthesis of homoallyl alcohols |
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Authors: | Ishiyama Tatsuo Ahiko Taka-aki Miyaura Norio |
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Institution: | Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan. ishiyama@org-mc.eng.hokudai.ac.jp |
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Abstract: | The addition of pinacol allylboronic esters to aromatic and aliphatic aldehydes smoothly occurred at -78 degrees C in toluene in the presence of a catalytic amount of AlCl3 or Sc(OTf)3 (10 mol %) to give the corresponding homoallyl alcohols in high yields. The reactions proceeded regio- and diastereospecifically, yielding the isomerically pure syn- and anti-homoallyl alcohols from (Z)- and (E)-allylboronic esters, respectively. The protocol was also applied to enantioselective reactions by using a chiral Lewis acid catalyst. |
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