Homochiral oxazolidin-2-ones and imidazolidin-2-ones by tandem nucleophilic addition–conjugate addition

…, ME González-Rosende, J Sepúlveda-Arques

Index: Ciclosi, Marco; Fava, Cristiana; Galeazzi, Roberta; Orena, Mario; Gonzalez-Rosende, Maria Eugenia; Sepulveda-Arques, Jose Tetrahedron Asymmetry, 2004 , vol. 15, # 12 p. 1937 - 1943

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Citation Number: 3

Abstract

Treatment of both primary alcohols 1a, b and secondary amines 1c, d, tethered to a Michael acceptor with (R)-phenylethyl isocyanate in the presence of DBU gave in good yield and high stereoselection diastereomeric mixtures of oxazolidin-2-ones 2a, b and 3a, b and imidazolidin-2-ones 2c, d and 3c, d, respectively. The cyclisation reaction was studied computationally by ab initio quantum mechanical methods. The observed stereoselectivity ...