A Mild Synthetic Procedure for the Preparation of N-Alkylated Sulfoximines

Carsten Bolm; Christian P. R. Hackenberger; Oliver Simić; Marinella Verrucci; Dirk Müller; Frank Bienewald

doi:10.1055/s-2002-28514

PAPER

A Mild Synthetic Procedure for the Preparation of N-Alkylated Sulfoximines

Carsten Bolm*, Christian P. R. Hackenberger, Oliver Simić, Marinella Verrucci, Dirk Müller, Frank Bienewald
Institut für Organische Chemie der RWTH Aachen, Professor-Pirlet-Strasse 1, 52056 Aachen, Germany
Fax: +49(241)8092391; e-Mail: Carsten.Bolm@oc.rwth-aachen.de;

Abstract

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Abstract

N-Alkylated sulfoximines have been synthesized in good yields by acylation of NH-sulfoximines followed by carbonyl reduction with complexed boranes. Enantiopure substrates react without racemization, and stereogenic centers originating from the acylating component are retained. If the acylation is performed by DCC coupling, this two-step procedure represents a rare example of a formal N-alkylation of sulfoximines under base-free conditions.

Keywords

acylation - borane - chirality - reduction - sulfoximine

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References

References and Notes

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The sulfoximines mentioned in entries 2 and 3 of Table [2] were prepared from TMS-protected (S)-S-methyl-S-phenyl-sulfoximine by metalation/alkylation sequence. Those shown in entries 4-8 (Table [2] ) were obtained by the procedure described in ref. [6] (MSH imination of the corresponding enantiopure sulfoxide).

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