203316-80-7Relevant academic research and scientific papers
Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis
Allen, Anna E.,MacMillan, David W. C.
supporting information; experimental part, p. 4260 - 4263 (2011/06/21)
The enantioselective α-arylation of aldehydes has been accomplished using diaryliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable α-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.
Phosphine-directed stereo- and regioselective Ni-catalyzed reactions of Grignard reagents with allylic ethers
Didiuk, Mary T.,Morken, James P.,Hoveyda, Amir H.
, p. 1117 - 1130 (2007/10/03)
Studies on the directed regio- and stereoselective Ni-catalyzed allylic substitution reactions involving methyl-and phenylmagnesium bromides and various acyclic and cyclic allylic ethers are reported. In the presence of a properly positioned internal Lewis base, C-C bonds can be formed catalytically and with excellent levels of selectivity. Internal chelation allows Ni-catalyzed C-C bond forming reactions that are otherwise non-selective, sluggish, or do not occur at all, to proceed to completion readily, in excellent yields, at ambient temperature and with high regio- and stereocontrol. Directed alkene isomerization highlights an especially attractive feature of the metal-catalyzed alkylation strategy: because the initial product contains a prostereogenic site that remains within reach of the internal Lewis base, it can be subjected to additional directed stereoselective manipulations.
