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Volumn , Issue 13, 2007, Pages 2121-2132

Advanced procedure for the preparation of cis-1,2-dialkylcyclopropanols - Modified ate complex mechanism for titanium-mediated cyclopropanation of carboxylic esters with Grignard reagents

Author keywords

Carboxylic esters; Cyclopropanols; Reaction mechanisms; Titanacyclopropanes; Titanium

Indexed keywords


EID: 34250654164     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601035     Document Type: Article
Times cited : (27)

References (42)
  • 16
    • 0029161631 scopus 로고    scopus 로고
    • For the formation of trans-1,2-disubstituted cyclopropanols as major products in reactions between esters and alkoxytitanacyclopropane reagents bearing functional substituents, see: a A. Kasatkin, F. Sato, Tetrahedron Lett. 1995, 36, 6079-6082;
    • For the formation of trans-1,2-disubstituted cyclopropanols as major products in reactions between esters and alkoxytitanacyclopropane reagents bearing functional substituents, see: a) A. Kasatkin, F. Sato, Tetrahedron Lett. 1995, 36, 6079-6082;
  • 28
    • 34250642766 scopus 로고    scopus 로고
    • For a successful application of methylmagnesium bromide as a sacrificial agent in the titanium(IV) isopropoxide-mediated cyclopropanation of methyl hexanoate with ethylmagnesium bromide, see: A. I. Savchenko, Dissertation, Belarusian State University, Minsk, 1995, p. 57.
    • For a successful application of methylmagnesium bromide as a sacrificial agent in the titanium(IV) isopropoxide-mediated cyclopropanation of methyl hexanoate with ethylmagnesium bromide, see: A. I. Savchenko, Dissertation, Belarusian State University, Minsk, 1995, p. 57.
  • 30
    • 34250639459 scopus 로고    scopus 로고
    • The putative titanium ate complex intermediates could also be involved in various ligand-exchange reactions with magnesium alkoxides or solvent, as well as in the formation of associates.[21] These processes are not discussed here for reasons of space
    • [21] These processes are not discussed here for reasons of space.
  • 31
    • 34250641955 scopus 로고    scopus 로고
    • A similar result was obtained when methylmagnesium iodide and n-propylmagnesium bromide were added sequentially to a mixture of ester 2a and titanium(IV) isopropoxide.
    • A similar result was obtained when methylmagnesium iodide and n-propylmagnesium bromide were added sequentially to a mixture of ester 2a and titanium(IV) isopropoxide.
  • 32
    • 0030930261 scopus 로고    scopus 로고
    • The formation of oxatitanacyclopropane intermediates in reactions between titanium(II) alkoxides or aryloxides and carbonyl compounds has also been observed by other authors: a) M. G. Thorn, J. E. Hill, S. A. Waratuke, E. S. Johnson, P. E. Fanwick, I. P. Rothwell, J. Am. Chem. Soc. 1997, 119, 8630-8641;
    • The formation of oxatitanacyclopropane intermediates in reactions between titanium(II) alkoxides or aryloxides and carbonyl compounds has also been observed by other authors: a) M. G. Thorn, J. E. Hill, S. A. Waratuke, E. S. Johnson, P. E. Fanwick, I. P. Rothwell, J. Am. Chem. Soc. 1997, 119, 8630-8641;
  • 41
    • 34250613526 scopus 로고    scopus 로고
    • An excess of benzaldehyde was converted into benzyl alcohol under the reaction conditions, due to reduction with metal alkoxides
    • An excess of benzaldehyde was converted into benzyl alcohol under the reaction conditions, due to reduction with metal alkoxides.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.