Regio‐and Diastereoselective Functionalization of 3‐Amino‐hexahydrooxazoninones

Ben Schurgers, Johan Wouters, Ann De Blieck, Guy Van Lommen, Christel Menet, Guido Verniest

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Résumé

The regio- and diastereoselectivity of transformations of nine-membered lactams with a Z double bond in the cyclic tether towards building blocks for medicinal chemistry was evaluated. To this end, 3-aminohexahydrooxazoninones were synthesized using a standard ring-closing metathesis (RCM) approach of easily available O,N-bisallylated serine derivatives. The obtained Z double bond in the medium sized lactam was used as a handle to evaluate the stereoselectivity of electrophile induced transformations. It was shown that dibromination and electrophilic activation by NBS followed by attack of O-nucleophiles proceeded in a diastereoselective manner. Cyclization of obtained bromohydrins and face-selective epoxidation gave access to both diastereomers of the epoxidized lactams. Finally, a Heck-reaction of a bromobenzyl moiety at the lactam N-atom with the Z-double bond resulted in the diastereoselective formation of bicyclic bridged nine-membered lactams.

langue originaleAnglais
Pages (de - à)36-40
Nombre de pages5
journalEuropean Journal of Organic Chemistry
Volume2019
Numéro de publication1
Les DOIs
Etat de la publicationPublié - 10 janv. 2019

Financement

The authors are indebted to the Agency for Innovation by Science and Technology (IWT) and Galapagos NV for financial sup- port. GV also is indebted to Vrije Universiteit Brussel (VUB, ZAP starting grant) for financial support. The authors thank Nikolay-Tumanov (PC2 platform at UNamur) for data collection.

Bailleurs de fondsNuméro du bailleur de fonds
Agency for Innovation by Science and Technology
Galapagos NV
Agentschap voor Innovatie door Wetenschap en Technologie

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