Expeditious formal synthesis of (±)-epibatidine using diastereoselective bromohydroxylation of aminocyclohexene derivatives

DOI: 10.1016/S0040-4039(98)01017-X

Source and publish data:

Tetrahedron Letters p. 5181 - 5184 (1998)

Update date:2022-08-12

Topics:

Authors:

Cabanal-Duvillard, Isabelle

Berrien, Jean-Francois

Royer, Jacques

Husson, Henri-Philippe

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Article abstract of DOI:10.1016/S0040-4039(98)01017-X

Bromination and bromohydroxylation of oxazolidinones derived from cyclohexadiene have been studied in order to synthetize (±)-epibatidine 18. Bromohydroxylation of compound 2 led to a polyfunctionalized halohydrin 11a which could be further cyclized to azabicyclo[2.2.1]heptan-2-one 16 already described as a precursor of epibatidine 18.

Full text of DOI:10.1016/S0040-4039(98)01017-X

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