174875-26-4Relevant academic research and scientific papers
Synthesis of bicyclic guanidines from pyrrolidin-2-one
Louwrier, Saskia,Tuynman, Antonin,Hiemstra, Henk
, p. 2629 - 2646 (1996)
The syntheses of three bicyclic guanidines as model compounds for the guanidine alkaloid ptilomycalin A are described. The guanidines are prepared from pyrrolidin-2-one via an N-acyliminium ion coupling reaction with silyl enol ethers and a direct guanylation with bis-Boc-thiourea and HgCl2 as the key steps.
Microwave-assisted tandem cross metathesis intramolecular Aza-Michael reaction: An easy entry to cyclic β-amino carbonyl derivatives
Fustero, Santos,Jimenez, Diego,Sanchez-Rosello, Maria,Del Pozo, Carlos
, p. 6700 - 6701 (2008/02/04)
Hoveyda-Grubbs catalyst in combination with BF3·OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of β-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched ∞-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process. Copyright
