Preparation of 2,3-trans-substituted piperidines from optically active β-amino-α-methylene esters: Synthesis of optically active (2S,3R)-(−)-epi-CP-99,994-Science-Chemical Encyclopedia-lookchem

Preparation of 2,3-trans-substituted piperidines from optically active β-amino-α-methylene esters: Synthesis of optically active (2S,3R)-(−)-epi-CP-99,994
Add time:08/29/2019 Source:sciencedirect.com

Chiral 2,3-trans-substituted piperidines were readily prepared in three steps from β-amino-α-methylene esters, which were prepared by the Michael/Mannich domino reaction of chiral sulfinimines. Hydrogenation of the N-tosyl-2-aryl-1,2,5,6-tetrahydropyridine intermediates took place smoothly in the presence of a Pd/C catalyst to give trans-2,3-disubstituted piperidines in good yields and in a highly stereoselective manner. The total synthesis of optically active (2S,3R)-(−)-epi-CP-99,994 was achieved in six-steps from an unsaturated piperidine.

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