Regio-selective synthesis of 1, 2-aminoalcohols from epoxides and chlorohydrins

…, V Torlikonda, SG Manjunatha, S Ramasubramanian…

Index: Murugan, Andiappan; Kadambar, Vasantha Krishna; Bachu, Sreekanth; Rajashekher Reddy; Torlikonda, Venkatarao; Manjunatha, Sulur G.; Ramasubramanian, Sridharan; Nambiar, Sudhir; Howell, Gareth P.; Withnall, Jane Tetrahedron Letters, 2012 , vol. 53, # 43 p. 5739 - 5741

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Abstract

1,2-Aminoalcohols are important building blocks in the synthesis of natural products, pharmaceuticals, and other materials. 1 Generally, these 1,2-aminoalcohols are prepared by nucleophilic ring opening of epoxides with nitrogen based nucleophiles. 2, 3, 4 and 5 Simple ammonolysis of epoxides 1 (Scheme 1) is one of the most commonly used methods 6 but frequently suffers from poor regio-selectivity (2 vs 3) and over alkylation (4). ... To circumvent these ...