97879-03-3Relevant academic research and scientific papers
Potassium tert-Butoxide-Catalyzed Synthesis of α-Methylene-β-Lactams from Propiolamides
Claus, Angelica R.,Goulart, Tales A. C.,Back, Davi F.,Zeni, Gilson
, p. 2180 - 2187 (2021/07/22)
We reported herein the regio- and stereoselective synthesis of α-methylene-β-lactams via a 4-exo-dig-cyclization of N-benzyl-N-methyl-propiolamides catalyzed by a base. The experimental evidence suggests that this transformation proceeds via a concerted ionic cyclization with a carbon nucleophilic addition to the carbon-carbon triple bond, followed by protonation of the vinyl species promoted by tert-butanol. The obtained α-methylene-β-lactams were suitable substrates for the Heck coupling conditions affording the corresponding products via carbon-carbon bond formation.
Iron(II) vinylidenes and chromium carbene complexes in β-lactam synthesis
Barrett, Anthony G. M.,Mortier, Jacques,Sabat, Michal,Sturgess, Michael A.
, p. 2553 - 2561 (2008/10/08)
Reaction of the chromium carbene 7 with toluene-4-sulfonyl chloride and the imine 8a gave 9a (26%). Alternatively reactions of the cationic iron(II) vinylidene reagents 20a,b, and 23a-d with the imines 8a-d and 2-thiazolines 28a-c gave the corresponding azetidinylidene complexes 21a,b, 24a-f, and 29a-d (11-82%). Subsequent oxidation of these complexes using iodosobenzene, pyridine N-oxide, bromine, air, or tetrabutylammonium nitrite gave the monocyclic or bicyclic β-lactams 10a-c, 25a-d, and 30a-c (8-97%).
CYCLOADDITION REACTIONS OF CATIONIC IRON VINYLLIDENE COMPLEXES
Barrett, Anthony G.M.,Sturgess, Michael A.
, p. 3811 - 3814 (2007/10/02)
Complexes (Ph3P)(Cp)(OC)Fe+=C=CR12BF4- underwent cycloaddition reactions with the imines MeN=CHR2 to give the corresponding cationic iron (II) 2-azetinylidene adducts.
