Titanium-mediated diastereoselective formation of (E)-2-alkyl-1-ethenylcyclopropanols from beta-haloesters

Authors
Sylvestre, I Ollivier, J Salaun, J
Citation
I. Sylvestre et al., Titanium-mediated diastereoselective formation of (E)-2-alkyl-1-ethenylcyclopropanols from beta-haloesters, TETRAHEDR L, 42(30), 2001, pp. 4991-4994
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
30
Year of publication
2001
Pages
4991 - 4994
Database
ISI
SICI code
0040-4039(20010723)42:30<4991:TDFO(>2.0.ZU;2-P
Abstract
The titanium(IV)-mediated cyclopropanation of ethyl beta -chloropropionate by Grignard reagents and in situ tosylation, followed by base-induced dehyd rochlorination provided diastereoselectivity pure (E)-2-alkyl-1-ethenyl-1-( tosyloxy)cyclopropanes. suitable precursors of 1,1-ethyleneallylmetal speci es of significant synthetic potential. (C) 2001 Elsevier Science Ltd. All r ights reserved.