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Addition of tert-butylcuprate to (2S)-N-acyl-Δ-dehydroprolinates as a diastereoselective synthetic procedure for obtaining (2S,5S)-5-tert-butylproline |
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| Authors: | Erik AA Wallén Johannes AM Christiaans Jukka Gynther Jouko Vepsäläinen |
| Institution: | a Department of Pharmaceutical Chemistry, University of Kuopio, PO Box 1627, FIN-70211 Kuopio, Finland b Department of Chemistry, University of Kuopio, PO Box 1627, FIN-70211 Kuopio, Finland c Finncovery Ltd., Kuopio, Finland |
| Abstract: | The synthesis of (2S,5S)-Boc-5-tert-butylproline ethyl ester via the addition of tert-butylcuprate to (2S)-N-Boc-Δ5-dehydroproline ethyl ester, formed from (2S)-N-Boc-5-methoxyproline ethyl ester, gives an excellent yield of 94% and a high diastereoselectivity (2S,5S):(2S,5R) 78:22. This synthesis opens up a new synthetic route to (2S,5S)-5-tert-butylproline, which is a useful, conformationally rigid, analogue of l-proline. |
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