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. 2011 Apr 15;76(8):2635-47.
doi: 10.1021/jo1025767. Epub 2011 Mar 16.

Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines

Marina Martjuga  1 , Sergey Belyakov, Edvards Liepinsh, Edgars Suna
Affiliations

Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines

Marina Martjuga et al. J Org Chem. .

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.

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