Synthesis of Cyclohexenylamines by Ring Closing Metathesis

Martin E. Maier; Tzvetelina Lapeva

doi:10.1055/s-1998-1789

Synlett 1998; 1998(8): 891-893
DOI: 10.1055/s-1998-1789

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Synthesis of Cyclohexenylamines by Ring Closing Metathesis

Martin E. Maier^* , Tzvetelina Lapeva

^*Martin-Luther-Universität Halle-Wittenberg, Fachbereich Chemie, Institut für Organische Chemie, Kurt-Mothes-Str. 2, 06120 Halle (Saale), Germany; Fax (+ 49)7071 29 5137; E-mail: martin.e.maier@uni-tuebingen.de

Abstract

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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.

ring closing metathesis - epibatidine - cyclohexenyl amine

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