Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds
A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp3)–H bond activation in the hydrocarbon was the turnover-limiting step and the in-situ formed [Co(III)]Ot-Bu did not engage in hydrogen atom abstraction (HAA) of a C–H bond. This protocol was successfully incorporated into a synthetic pathway to β-damascenone that avoided the use of NBS.
Diastereoselectivity in the epoxidation of substituted cyclohexenes by dimethyldioxirane
Three series of compounds based on the cyclohexene framework have been epoxidized by dimetbyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition there is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole - dipole influences on the epoxide stereochemistry.
Murray, Robert W.,Singh, Megh,Williams, Brian L.,Moncrieff, Hazel M.
p. 1830 - 1841
(2007/10/03)
Reactions du n=chloroparatoluenesulfonamidate de sodium (chloramine t) sur les olefines en miliu acide organique
Vic. chloro-acetoxy and vic. chloro-tosylamino alcanes are the main products of the electrophilic reaction of chloramine T on olefins in acetic acid. The stereochemistry of the acetoxy chloration of the 2-butenes and cyclohexene is trans.
Damin, Bernard,Garapon, Jacques,Sillion, Bernard
p. 1709 - 1710
(2007/10/02)
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