Synlett 2002(10): 1733-1735
DOI: 10.1055/s-2002-34219
LETTER
© Georg Thieme Verlag Stuttgart · New York

Inter- and Intramolecular Additions of 1-Alkenylboronic Acids or Esters to Aldehydes and Ketones Catalyzed by Rhodium(I) Complexes in Basic, Aqueous Solutions

Akinori Takezawa, Kenji Yamaguchi, Toshimichi Ohmura, Yasunori Yamamoto, Norio Miyaura*
Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
Fax: +81(11)7066561; e-Mail: miyaura@org-mc.eng.hokudai.ac.jp;
Further Information

Publication History

Received 23 August 2002
Publication Date:
23 September 2002 (online)

Abstract

Grignard-type addition reaction of 1-alkenylboronic acids or their esters to aldehydes or ketones were carried out in aqueous MeOH or DME in the presence of KOH (1 equivalent) and an RhCl(dppf) or Rh(OH)(dppf) catalyst (3 mol%). The utility of the protocol was demonstrated in the corresponding intramolecular reaction giving cyclic homoallylic alcohols.