17783-69-6Relevant academic research and scientific papers
Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles
Alexanian, Erik J.,Tercenio, Quentin D.
supporting information, p. 7215 - 7219 (2021/09/22)
The stereospecific cross-coupling of easily accessed electrophiles holds significant promise in the construction of C-C bonds. Herein, we report a nickel-catalyzed reductive coupling of allyl alcohols with chiral, nonracemic alkyl tosylates. This cross-coupling delivers valuable allylation products with high levels of stereospecificity across a range of substrates. The catalytic system consists of a simple nickel salt in conjunction with a commercially available reductant and importantly represents a rare example of a cross-coupling involving the C-O bonds of two electrophiles.
Directionality of Proton Transfer in Solutions. Three Systems of Known Angularity
Menger, F. M.,Chow, J. F.,Kaiserman, H.,Vasquez, P. C.
, p. 4996 - 5002 (2007/10/02)
Three compounds were synthesized each possessing rigid carbon frameworks that hold an oxygen base near a mobile C-H proton in well-defined angular and distance relationships: 2-iodo-4-hydroxyindan, endo-5-hydroxybicycloheptan-2-one, and endo-2-hydroxy-exo-6-bromomethylheptane.Effective proton transfer was detected with the second and third compounds but not the first.The data suggest that C-to-O proton transfer with severely bent O/H/C angles (106 deg) is permissible if the O-H distance is less than the sum of the van der Waals radii. "Long distance" catalysis at active sites of enzymes appears unlikely.
