Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines |
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Authors: | Martjuga Marina Belyakov Sergey Liepinsh Edvards Suna Edgars |
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Institution: | Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia. |
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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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