A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methanoamino acids

Authors
Kozyrkov, YY Pukin, A Kulinkovich, OG Ollivier, J Salaun, J
Citation
Yy. Kozyrkov et al., A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methanoamino acids, TETRAHEDR L, 41(33), 2000, pp. 6399-6402
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
33
Year of publication
2000
Pages
6399 - 6402
Database
ISI
SICI code
0040-4039(20000812)41:33<6399:ACATS1>2.0.ZU;2-#
Abstract
The diastereoselective titanium(IV)-mediated cyclopropanation of ethyl 3,3- diethoxypropionate by Grignard reagents, followed by modified Knoevenagel c ondensation with malonic acid under microwave irradiation, allow the prepar ation of (E)-1-(1-alkenyl)cyclopropanol derivatives, suitable precursors of pi-1,1-dimethyleneallylmetal species. The azidation of such complexes, fol lowed by a reduction-oxidation sequence led to pure (E)-2,3-methanoamino ac ids. (C) 2000 Elsevier Science Ltd. All rights reserved.