Nitroalkenes as electrophiles in the asymmetric Michael reaction involvingchiral imines enamino esters

Authors
Thominiaux, C Rousse, S Desmaele, D d'Angelo, J Riche, C
Citation
C. Thominiaux et al., Nitroalkenes as electrophiles in the asymmetric Michael reaction involvingchiral imines enamino esters, TETRAHEDR-A, 10(10), 1999, pp. 2015-2021
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
10
Year of publication
1999
Pages
2015 - 2021
Database
ISI
SICI code
0957-4166(19990521)10:10<2015:NAEITA>2.0.ZU;2-O
Abstract
Addition of 2-nitropropene to the chiral imine derived from 2-methylcyclope ntanone and (S)-1-phenylethylamine furnished the expected Michael adduct. T he latter compound was then efficiently converted into (R)-pentalenone thro ugh a Nef reaction. Condensation of the enamino ester derived from 2-carbet hoxycyclopentanone and (S)-1-phenylethylamine with 1-nitropropene gave with excellent diastereo- and enantioselectivity the corresponding Michael addu ct. (C) 1999 Elsevier Science Ltd. All rights reserved.