119341-75-2Relevant articles and documents
Effect of water on the functionalization of substituted anisoles with iodine in the presence of F-TEDA-BF4 or hydrogen peroxide
Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
, p. 1027 - 1032 (2006)
Water was found to be a convenient reaction medium for functionalization of substituted anisoles using iodine in the presence of Selectfluor F-TEDA-BF 4 or hydrogen peroxide as mediators and oxidizers. Two types of functionalization were observ
Asymmetric synthesis of (: S)-phenylacetylcarbinol-closing a gap in C-C bond formation
Sehl, Torsten,Bock, Saskia,Marx, Lisa,Maugeri, Zaira,Walter, Lydia,Westphal, Robert,Vogel, Constantin,Menyes, Ulf,Erhardt, Martin,Müller, Michael,Pohl, Martina,Rother, D?rte
supporting information, p. 380 - 384 (2017/08/14)
(S)-Phenylacetylcarbinol [(S)-PAC] and its derivatives are valuable intermediates for the synthesis of various active pharmaceutical ingredients (APIs), but their selective synthesis is challenging. As no highly selective enzymes or chemical catalysts were available, we used semi-rational enzyme engineering to tailor a potent biocatalyst to be >97% stereoselective for the synthesis of (S)-PAC. By optimizing the reaction and process used, industrially relevant product concentrations of >48 g L-1 (up to 320 mM) were achieved. In addition, the best enzyme variant gave access to a broad range of ring-substituted (S)-PAC derivatives with high stereoselectivity, especially for meta-substituted products.
Biocatalytic route to chiral acyloins: P450-catalyzed regio- and enantioselective α-hydroxylation of ketones
Agudo, Rubén,Roiban, Gheorghe-Doru,Lonsdale, Richard,Ilie, Adriana,Reetz, Manfred T.
, p. 950 - 956 (2015/01/30)
P450-BM3 and mutants of this monooxygenase generated by directed evolution are excellent catalysts for the oxidative α-hydroxylation of ketones with formation of chiral acyloins with high regioselectivity (up to 99%) and enantioselectivity (up to 99% ee). This constitutes a new route to a class of chiral compounds that are useful intermediates in the synthesis of many kinds of biologically active compounds.
I2- or NBS-catalyzed highly efficient α-hydroxylation of ketones with dimethyl sulfoxide
Liang, Yu-Feng,Wu, Kai,Song, Song,Li, Xinyao,Huang, Xiaoqiang,Jiao, Ning
supporting information, p. 876 - 879 (2015/04/14)
An efficient method for the direct preparation of high synthetic valuable α-hydroxycarbonyls is described. The simple and readily available I2 or NBS was used as catalyst. DMSO acts as the oxidant, oxygen source, and solvent. A diverse range of tertiary Csp3-H bonds as well as more challenging secondary Csp3-H bonds could be hydroxylated in this transformation. The reaction is mild, less toxic and easy to perform.