1154743-87-9Relevant academic research and scientific papers
Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols
Shi, Chang-Yun,Yin, Liang,Zhang, Qi,Zhou, Si-Wei
, p. 26351 - 26356 (2021/11/09)
By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.
Highly regio- and stereoselective addition of organolithium reagents to extended conjugate amides using (S,S)-(+)-pseudoephedrine as chiral auxiliary
Ocejo, Marta,Carrillo, Luisa,Badia, Dolores,Vicario, Jose L.,Fernandez, Naiara,Reyes, Efraim
supporting information; experimental part, p. 4404 - 4407 (2009/09/06)
(Chemical Equation Presented) The conjugate addition of organolithium reagents to polyunsaturated conjugate amides containing (S,S)-(+)- pseudoephedrine as chiral auxiliary has been studied in detail. The reaction proceeded with good 1,4-selectivity and e
