Asymmetric Synthesis of 1, 3-Diamines. II: Diastereoselective Reduction of Atropisomeric N-tert-Butanesulfinylketimines

M Martjuga, S Belyakov, E Liepinsh…

Index: Martjuga, Marina; Shabashov, Dmitry; Belyakov, Sergey; Liepinsh, Edvards; Suna, Edgars Journal of Organic Chemistry, 2010 , vol. 75, # 7 p. 2357 - 2368

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Citation Number: 10

Abstract

Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d− f. The free energy of activation for atropisomerization of sulfinylimines 4d− f in THF-d 8 was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.