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Microwave-Assisted Solvent-Free Synthesis of Enantiomerically Pure N-(tert-Butylsulfinyl)imines

Juan F. Collados, Estefanía Toledano, David Guijarro* and Miguel Yus

*Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain, Email: dguijarroua.es

J. F. Collados, E. Toledano, D. Guijarro, M. Yus, J. Org. Chem., 2012, 77, 5744-5750.

DOI: 10.1021/jo300919x (free Supporting Information)


Abstract

Microwave-promoted condensation of carbonyl compounds with (R)-2-methylpropane-2-sulfinamide under solvent-free conditions in the presence of Ti(OEt)4 enables a simple, environmentally friendly synthesis of optically pure N-(tert-butylsulfinyl)imines. Sulfinyl aldimines can be prepared with excellent yields and purities in only 10 min, whereas the reaction time for the preparation of ketimines has been extended to 1 h.

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Key Words

Imines, Microwave Synthesis


ID: J42-Y2012-2200