23809-98-5Relevant articles and documents
Direct Electrophilic C?H Alkynylation of Unprotected 2-Vinylanilines
Caspers, Lucien D.,Finkbeiner, Peter,Nachtsheim, Boris J.
supporting information, p. 2748 - 2752 (2017/03/08)
Unprotected aromatic amines can be used as directing groups in metal-catalyzed C?H alkynylations of alkenes. By using low amounts of an IrIIIcatalyst in combination with alkynylbenziodoxolones as electrophilic alkyne-transfer reagents, highly desirable 1,3-enynes were isolated in excellent yields of up to 98 % with Z stereoselectivity. A broad substrate scope as well as the high synthetic utility of the 1,3-enynes render this new method an efficient approach for the synthesis of five- and six-membered heterocycles. Further derivatizations of the 1,3-enynes to highly substituted quinolines through AuI- and N-bromosuccinimide-mediated exo-dig cyclizations were demonstrated.
Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis
Featherston, Aaron L.,Miller, Scott J.
supporting information, p. 4871 - 4874 (2016/10/04)
We report the synthesis of phenylalanine-derived trifluoromethyl ketones for the in situ generation of dioxiranes for the purpose of oxidation catalysis. The key features of this synthesis include the use of a masked ketone strategy and a Negishi cross-coupling to access the parent amino acid. The derivatives can be readily incorporated into a peptide for use in oxidation chemistry and exhibit good stability and reactivity.
