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2005
Pyridine derivatives
R 0380
Palladium-Catalyzed C—C Coupling Reactions in the Enantioselective Synthesis
2,4-Disubstituted 4,5-Dehydropiperidines Using Galactosylamine as a Stereo25- 137 of
differentiating Auxiliary. — The stereoselective synthesis of enantiopure 4-substituted piperidine derivatives is presented. The pathway involves a highly diastereoselective
tandem Mannich—Michael reaction of galactosyl aldimines (I) to give dihydropyridinones (III) followed by Suzuki—Miyaura coupling of arylboronic acids (VI) to the corresponding enol triflates (V) to install the 4-substituent. — (KNAUER, S.; KUNZ*,
H.; Tetrahedron: Asymmetry 16 (2005) 2, 529-539; Inst. Org. Chem.,
Johannes-Gutenberg-Univ., D-55128 Mainz, Germany; Eng.) — Mischke
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