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Titolo:
Diastereoselective Lewis acid mediated hydrophosphonylation of heterocyclic imines: a stereoselective approach towards alpha-amino phosphonates
Autore:
Schlemminger, I; Willecke, A; Maison, W; Koch, R; Lutzen, A; Martens, J;
Indirizzi:
Univ Oldenburg, Dept Chem, D-26111 Oldenburg, Germany Univ Oldenburg Oldenburg Germany D-26111 hem, D-26111 Oldenburg, Germany
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 21, , anno: 2001,
pagine: 2804 - 2816
SICI:
1472-7781(20011107):21<2804:DLAMHO>2.0.ZU;2-N
Fonte:
ISI
Lingua:
ENG
Soggetto:
HETEROBIMETALLIC LANTHANOID COMPLEXES; ORGANIC PHOSPHORUS-COMPOUNDS; STATE ANALOG INHIBITORS; ASYMMETRIC-SYNTHESIS; ORGANOPHOSPHORUS COMPOUNDS; AMINOPHOSPHONIC ACIDS; ENANTIOSELECTIVE HYDROPHOSPHONYLATION; THIAZOLIDINE-4-CARBOXYLIC ACIDS; ENANTIOPURE SULFINIMINES; BIOLOGICAL-ACTIVITY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
95
Recensione:
Indirizzi per estratti:
Indirizzo: Martens, J Univ Oldenburg, Dept Chem, POB 2503, D-26111 Oldenburg, GermanyUniv Oldenburg POB 2503 Oldenburg Germany D-26111 urg, Germany
Citazione:
I. Schlemminger et al., "Diastereoselective Lewis acid mediated hydrophosphonylation of heterocyclic imines: a stereoselective approach towards alpha-amino phosphonates", J CHEM S P1, (21), 2001, pp. 2804-2816

Abstract

The synthesis of new chiral a-amino phosphonates by the Lewis acid mediated addition or bisesters or phosphonic acid to 3-thiazolines (2,5-dihydro-1,3-thiazoles), is described. The diastereoselectivity of the reaction using chiral reactants was systematically investigated. The chiral BINOL-phosphonate 1 was found to be a highly stereoselective phosphonylating agent towards 3-thiazolines. Structural aspects of the resulting thiazolidinylphosphonates were studied by NMR and X-ray analyses. The role of the Lewis acid as aspatial mediator is discussed and a quantum chemical description of the Lewis acid mediated hydrophosphonylation presented.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 20/09/20 alle ore 07:47:07