4.8 Article

Stereloselective synthesis of 2,5,6-trisubstituted piperidines

Journal

ORGANIC LETTERS
Volume 4, Issue 12, Pages 2029-2031

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol025859v

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Funding

  1. NCRR NIH HHS [S10-RR13673] Funding Source: Medline
  2. NIGMS NIH HHS [GM60003] Funding Source: Medline
  3. FDA HHS [BM59384] Funding Source: Medline

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[GRAPHIC] A short and efficient synthesis of 2,5,6-trisubstituted piperidines was achieved by a combination of an aza-Achmatowicz oxidation of a furyl benzenesulfonamide, conjugate addition to the resulting 2H-pyridinone, and subsequent addition of various nucleophiles to a transient N-sulfonyliminium ion. The steric bulk of the tosyl group directs attack of the nucleophile from its opposite side, thereby leading to the formation of cis-substituted products.

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