101255-12-3Relevant articles and documents
Formation of o-Allyl- And Allenyl-Modified Amides via Intermolecular Claisen Rearrangement
Niu, Zhi-Jie,Li, Lian-Hua,Li, Xue-Song,Liu, Hong-Chao,Shi, Wei-Yu,Liang, Yong-Min
, p. 1315 - 1320 (2021/02/20)
We developed a new transition-metal-free intermolecular Claisen rearrangement process to introduce allyl and allenyl groups into the α position of tertiary amides. In this transformation, amides were activated by trifluoromethanesulfonic anhydride to produce the keteniminium ion intermediates that exhibit strong electrophilic activity. This atom-economical process delivers α position-modified amides under mild conditions in moderate to good yields and showcases a broad substrate compatibility.
Diastereoselective Syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate
Maligres,Upadhyay,Rossen,Cianciosi,Purick,Eng,Reamer,Askin,Volante,Reider
, p. 2195 - 2198 (2007/10/02)
Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employe