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Synlett 2001; 2001(10): 1569-1570
DOI: 10.1055/s-2001-17460
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Regio- and Stereoselective Addition of Grignard Reagents to N-Galactosyl-2-Pyridone: Synthesis of 4-Substituted 5,6-Didehydro-2-piperidinones

Markus Follmann* , Alexander Rösch, Ellen Klegraf, Horst Kunz
  • *Institut für Organische Chemie, Universität Mainz, 55099 Mainz, Germany; Fax + 49(6131)3 92 23 34; E-mail: hokunz@mail.uni-mainz.de
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Publication Date:
27 September 2001 (online)

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Grignard reagents add diastereo- and regioselectively to the γ-position of N-(2,3,4,6-tetra-O-pivaloyl-β-d-galactopyranosyl)-1,2-dihydro-pyridin-2-one in situ, when activated by trimethylsilyl trifluoromethanesulfonate yielding enantiomerically pure 4-substituted N-galactosyl-5,6-didehydro-2-piperidinones.

stereoselective conjugate addition - carbohydrate auxiliaries - 4-substituted piperidones - Grignard addition