88431-04-3Relevant academic research and scientific papers
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
supporting information, 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.
Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides
Maligres,Weissman,Upadhyay,Cianciosi,Reamer,Purick,Sager,Rossen,Eng,Askin,Volante,Reider
, p. 3327 - 3338 (2007/10/03)
Reaction of 2-alkyl-4-enamides with I+ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).
Asymmetric synthesis of intermediates for retroviral protease inhibitor compounds
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, (2008/06/13)
The disclosure describes an improved process for producing optically active compounds of Formula II or III, which compounds are useful as intermediates for preparing compounds active as inhibitors of retroviral protease enzymes: STR1 wherein R1
1,3-Asymmetric Induction: Highly Stereoselective Synthesis of 2,4-Trans-Disubstituted γ-Butyrolactones and γ-Butyrothiolactones
Tamaru, Yoshinao,Mizutani, Masato,Furukawa, Yutaka,Kawamura, Shin-ichi,Yoshida, Zen-ichi,et al.
, p. 1079 - 1085 (2007/10/02)
A novel 1,3-trans asymmetric induction has been observed for the halolactonization of α- and α,β-substituted γ,δ-unsaturated amides.The 1,3-trans selectivity is lost in the threo diastereomers of amides with β-OH or β-OAc substituent, due to the 1,2-cis d
