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

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

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 wi...

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Veröffentlicht in:Organic letters 2011-09, Vol.13 (17), p.4534-4537
Hauptverfasser: Arroyo, Yolanda, Sanz-Tejedor, M. Ascensión, Alonso, Inés, García-Ruano, José L
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemical synthesis
Amines - chemistry
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Quantum Theory
Stereoisomerism
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201696y