Download PDF
Synlett 2001; 2001(1): 0049-0052
DOI: 10.1055/s-2001-9707
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Regioselective Carbon-Carbon Bond Formation in Titanium Mediated Reaction of Ethylmagnesium Bromide with Allylic Alcohols and Allylic Ethers

Oleg G. Kulinkovich* , Oleg L. Epstein, Vladimir E. Isakov, Ekaterina A. Khmel'nitskaya
  • *Department of Organic Chemistry, Belarussian State University, 4, Skoriny av., Minsk, Belarus; Fax +375-17-226-4998; E-mail: kulinkovich@chem.bsu.unibel.by
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

In the presence of Ti(Oi-Pr)4 reaction of EtMgBr with allylic alcohols and allylic ethers affords the products of formal SN2′ substitution of hydroxy or alkoxy groups with ethyl groups in moderate to good yields and excellent regioselectivity. The mechanism of the reaction includes the formation of titanacyclopropanes as the key organometallic intermediates. Promoting action of EtMgBr on the process of C-C bond formation in the transformation of titanacyclopropane-olefin complex 5 into the titanacyclopentane at complex 6 is proposed.

titanium alkoxides - Grignard reagents - allylic compounds - alkylations - alkenes

      >