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Communication

Acceleration Effect of Lewis Acid in Allylboration of Aldehydes: Catalytic, Regiospecific, Diastereospecific, and Enantioselective Synthesis of Homoallyl Alcohols^†

Supporting Info

Tatsuo Ishiyama,* Taka-aki Ahiko, and Norio Miyaura*

Contribution from the Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan

J. Am. Chem. Soc., 2002, 124 (42), pp 12414–12415

DOI: 10.1021/ja0210345

Publication Date (Web): September 27, 2002

†

After our manuscript was submitted, we became aware of a related study by Hall: Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124. Published ASAP, September 6, 2002.

Corresponding author. E-mail: ishiyama@org-mc.eng.hokudai.ac.jp.

Abstract

The addition of pinacol allylboronic esters to aromatic and aliphatic aldehydes smoothly occurred at −78 °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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Published In Issue October 23, 2002
Received July 29, 2002

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Communication

Acceleration Effect of Lewis Acid in Allylboration of Aldehydes: Catalytic, Regiospecific, Diastereospecific, and Enantioselective Synthesis of Homoallyl Alcohols^†