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Titolo:
Diastereoselective synthesis of chiral amidophosphonates by 1,5-asymmetricinduction
Autore:
Castelot-Deliencourt, G; Roger, E; Pannecoucke, X; Quirion, JC;
Indirizzi:
INSA, IRCOF, CNRS, Lab Heterochim Organ Associe, F-76131 Mont St Aignan, France INSA Mont St Aignan France F-76131 socie, F-76131 Mont St Aignan, France
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 16, , anno: 2001,
pagine: 3031 - 3038
SICI:
1434-193X(200108):16<3031:DSOCAB>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
ASYMMETRIC-SYNTHESIS; PHOSPHONIC-ACIDS; ENANTIOSELECTIVE SUBSTITUTIONS; GRIGNARD-REAGENTS; BETA-LITHIATION; (-)-SPARTEINE; ANTAGONISTS; ADDITIONS; AMIDES; GABA;
Keywords:
alkylations; amides; asymmetric synthesis; Michael additions;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
30
Recensione:
Indirizzi per estratti:
Indirizzo: Quirion, JC INSA, IRCOF, CNRS, Lab Heterochim Organ Associe, 1 Rue Tesniere, F-76131 Mont St Aignan, France INSA 1 Rue Tesniere Mont St Aignan France F-76131 nan, France
Citazione:
G. Castelot-Deliencourt et al., "Diastereoselective synthesis of chiral amidophosphonates by 1,5-asymmetricinduction", EUR J ORG C, (16), 2001, pp. 3031-3038

Abstract

We have investigated two simple diastereoselective syntheses of substituted beta -amidophosphonates. The first one involved a Michael addition to alpha,beta -unsaturated amides 6 and 8a-d, derived from chiral amino alcohols,and permitted the preparation of alkyl-substituted derivatives 7 and 9a-d with high diastereoselectivities (up to 95%) with the aid of a 1,5-asymmetric induction, The second one, involving 1,5-inductive alkylation of chiral beta -amidophosphonates 14a-c, was promising in terms of the yields, but the diastereoselectivities were disappointing (up to 50%). Finally, removal of the chiral auxiliary afforded phosphonocarboxylic acid, able to provide access to a wide range of compounds of great interest for the synthesis of biologically active products.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/01/20 alle ore 21:40:02