Highly diastereoselective nucleophilic addition of organometallic reagentsto 2-pyrrolidinyl nitrones: a semiempirical approach

Authors
Merino, P Franco, S Gascon, JM Merchan, FL Tejero, T
Citation
P. Merino et al., Highly diastereoselective nucleophilic addition of organometallic reagentsto 2-pyrrolidinyl nitrones: a semiempirical approach, TETRAHEDR-A, 10(10), 1999, pp. 1867-1871
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
10
Year of publication
1999
Pages
1867 - 1871
Database
ISI
SICI code
0957-4166(19990521)10:10<1867:HDNAOO>2.0.ZU;2-E
Abstract
2-Pyrrolidinyl nitrones 1 and 2 derived from L-proline and trans-4-hydroxy- L-proline, respectively, undergo nucleophilic additions of Grignard reagent s and organolithium compounds with high syn selectivity, to yield enantiome rically pure pyrrolidinyl benzyl hydroxylamines. A rationale for the observ ed stereoselectivity based on semiempirical calculations is presented. (C) 1999 Elsevier Science Ltd. All rights reserved.