New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: Synthesis of the tricyclic core of (+/-)-martinellines

作者：Comesse Sebastien^*; Sanselme Morgane; Daich Adam

来源：Journal of Organic Chemistry, 2008, 73(14): 5566-5569.

DOI：10.1021/jo702752w

A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution is presented. This unprecedented tandem reaction between N-substituted alpha-bromoacetamides and Michael acceptors proceeds with good yields and excellent diastereoselectivity to provide the corresponding trisubstituted gamma-lactam systems. An application to the concise synthesis of the tricyclic core of martinelline alkaloids is also described.

• 出版日期2008-7-18