First Diels-Alder Cycloaddition ofN′-Oxazolyl-N,N-dimethylalkylamidines with Electron-Poor Dienophiles: Characterization of a Diastereoselective Pathway

Autor:	Jean Guillon, Jean-Michel Léger, Stéphane Massip, Corinne Thé, Céline Vidaillac, Jean-Pierre Monti, Christian Jarry
Rok vydání:	2002
Předmět:	Chemistry Stereochemistry Organic Chemistry Diels alder Regioselectivity Cycloaddition Diels–Alder reaction
Zdroj:	Synlett. :1249-1252
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-2002-32954
Popis:	Diels-Alder cycloaddition of N'-oxazolyl-N,N-dimethylalkylamidines la,b with electron-poor dienophiles were performed, leading to new 2-phenoxymethyl-6-formyl-2,3-dihydro-5H-oxazolo[3,2-a]pyrimidines and 2-phenoxymethyl-6-nitro-2,3-dihydro-5H-oxazolo[3,2-a]pyrimidines. The regio and endo diastereoselectivity of one [4+2] cycloadduct 4 was established through the single-crystal X-ray structure determination of 4a. The diastereoselectivity could be related to a potential it-stacking interaction.
Databáze:	OpenAIRE
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