Synthesis 2006(21): 3597-3604  
DOI: 10.1055/s-2006-942542
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Entry to Amino Sugars and Derivatives via Asymmetric Organo­catalytic Mannich Reactions

Dieter Enders*, Christoph Grondal, Marianna Vrettou
Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;
Further Information

Publication History

Received 19 May 2005
Publication Date:
02 August 2006 (online)

Abstract

An efficient biomimetic C3+Cn entry to amino sugars and derivatives via a direct asymmetric organocatalytic Mannich methodology employing 2,2-dimethyl-1,3-dioxan-5-one as a dihydroxyacetone phosphate equivalent and N-PMP or N-Boc protected imines has been developed. The Mannich bases were obtained in high diastereo- and enantiomeric excesses (78% to >99% de, 81-98% ee) and were further elaborated using diastereoselective reduction protocols, as well as via diastereoselective direct reductive amination­ reactions.

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