A Single??Step Synthesis of 4??Oxazolin??2??ones and Their Use in the Construction of Polycyclic Structures Bearing Quaternary Stereocenters

…, R Martínez??Palou, A Fuentes??Benites…

Index: Santoyo, Blanca M.; Gonzalez-Romero, Carlos; Merino, Omar; Martinez-Palou, Rafael; Fuentes-Benites, Aydee; Jimenez-Vazquez, Hugo A.; Delgado, Francisco; Tamariz, Joaquin European Journal of Organic Chemistry, 2009 , # 15 p. 2505 - 2518

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Citation Number: 7

Abstract

Abstract A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of α-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the ...