915092-88-5Relevant academic research and scientific papers
New bioorganic reagents: Evolved cyclohexanone monooxygenase - Why is it more selective?
Kayser, Margaret M.,Clouthier, Christopher M.
, p. 8424 - 8430 (2006)
Four mutants of the cyclohexanone monooxygenase (CHMO) evolved as catalysts for Baeyer-Villiger oxidation of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified. The most important, however, is the finding that, in a number of cases, a mutant with a single exchange, Phe432Ser, was shown to be as robust and more selective as a catalyst than the wild-type CHMO. All biotransformations were performed on a laboratory scale, allowing full characterization of the products. The absolute configurations of two products were established. A model suggesting a possible role of the 432 serine residue in enantioselectivity control is proposed.
Hydroxyl group-assisted palladium-catalyzed lactonization of homoallylic alcohols
Huang, Liangbin,Wang, Qian,Wu, Wanqing,Jiang, Huanfeng
, p. 561 - 566 (2014/03/21)
A convenient and highly efficient synthesis of α-methylene-γ- lactones through the palladium(II)-catalyzed lactonization of homoallylic alcohols with alkynamides has been reported. The hydroxyl group in the terminal olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination. This process provides a route to construct naturally occurring biologically multifunctional α-methylene-γ- lactones. The time has come to.i?lactonize: α-Methylene- γ-lactones are synthesized through the PdII-catalyzed lactonization of homoallylic alcohols with alkynamides. The hydroxyl group in the terminal olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination. This provides a route towards naturally occurring biologically multifunctional α-methylene- γ-lactones. Copyright
