Synthesis of Cyclohexenylamines by Ring Closing Metathesis

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Abstract
Starting from 5-pentenaldehyde 1, the 1-allyl-4-pentenylamines 2a-d were prepared. The ring closing metathesis reaction of these dienes using the Grubbs catalyst 3 gave the corresponding cyclohexenylamines 4a, b and 4d in high yield. The secondary amine 2c was recovered unchanged. This route to compound 4d represents a formal total synthesis of the alkaloid epibatidine. In additon, 4b was transformed by electrophilic transannular cyclization to the bicyclic urethanes 5a and 5b.

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