Volume 38, Issue 1-2 pp. 195-197
Communication

Enantioselective Synthesis of β-Amino Sulfones by aza-Michael Addition to Alkenyl Sulfones

Dieter Enders

Dieter Enders

Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-52074 Aachen (Germany), Fax: (+49) 241-888-8127

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Stephan F. Müller

Stephan F. Müller

Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-52074 Aachen (Germany), Fax: (+49) 241-888-8127

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Gerhard Raabe

Gerhard Raabe

Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-52074 Aachen (Germany), Fax: (+49) 241-888-8127

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Abstract

Regardless of whether SAMP or RAMBO (or their enantiomers RAMP or SAMBO) are used, the asymmetric synthesis of N-protected β-amino sulfones 4 by conjugate addition of a chiral nitrogen nucleophile (S)-1 (SAMP) or (R,R,R)-2 (RAMBO) to (E)-alkenyl sulfones 3 proceeds with high enantiomeric excesses. The title compounds are obtained after removal of the chiral auxiliary by reductive N−N bond cleavage.

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