Tatsuo Ishiyama*, Taka-aki Ahiko, N. Miyaura
Sep 27, 2002
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Influential Citations
104
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Journal
Journal of the American Chemical Society
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.