Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Efficient Entry to Amino Sugars and Derivatives via Asymmetric Organocatalytic Mannich Reactions Dieter Enders*, Christoph Grondal, Marianna VrettouInstitut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, GermanyFax: +49(241)8092127; e-Mail: enders@rwth-aachen.de; Recommend Article Abstract Buy Article All articles of this category 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. Key words organocatalysis - Mannich reaction - amino sugars - asymmetric synthesis - reductive amination Full Text References References 1a List B. Tetrahedron 2002, 58: 5573 1b List B. Acc. Chem. Res. 2004, 37: 548 1c Notz W. Tanaka F. Barbas CF. Acc. Chem. Res. 2004, 37: 580 2a Arend M. Westermann B. Risch N. Angew. Chem. Int. Ed. 1998, 37: 1044 ; Angew. Chem. 1998, 110, 1096 2b Kobayashi S. Ishitani H. Chem. Rev. 1999, 99: 1069 3a For a first asymmetric Mannich reaction, see: Kober R. Papadopoulos K. Miltz W. Enders D. Steglich W. Tetrahedron 1985, 41: 1693 3b For a first practical asymmetric Mannich reaction, see: Enders D. Ward D. Adam J. Raabe G. Angew. Chem., Int. Ed. Engl. 1996, 35: 981 ; Angew. Chem. 1996, 108, 1059 4a List B. J. Am. Chem. Soc. 2000, 122: 9336 4b List B. Pojarliev P. Biller WT. Martin HJ. J. Am. Chem. Soc. 2002, 124: 827 5a Notz W. Sakthivel K. Bui T. Zhong G. Barbas CF. Tetrahedron Lett. 2001, 42: 199 5b Córdova A. Notz W. Zhong G. Betancort JM. Barabs CF. 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