ol201696y_si_001.cif (15.21 kB)

Synthesis of Optically Pure vic-Sulfanyl Amines Mediated by a Remote Sulfinyl Group

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posted on 02.09.2011, 00:00 by Yolanda Arroyo, M. Ascensión Sanz-Tejedor, Inés Alonso, José L. García-Ruano
Enantiomerically pure syn-1,2-diaryl-1,2-sulfanylamine derivatives can be obtained in a completely stereoselective manner by reaction of the benzylcarbanion Li-(S)-1 with N-phenyl (or PMP)-arylidene aldimines and further desulfinylation with t-BuLi. Theoretical studies at the DFT (mPW1PW91) level with the CPCM model, by using the Gaussian09 program, provide a good explanation for the stereochemical results.