17375-96-1Relevant articles and documents
One-Pot Enzymatic-Chemical Cascade Route for Synthesizing Aromatic α-Hydroxy Ketones
Wang, Lei,Song, Wei,Wang, Binju,Zhang, Yan,Xu, Xin,Wu, Jing,Gao, Cong,Liu, Jia,Chen, Xiulai,Chen, Jinghua,Liu, Liming
, p. 2808 - 2818 (2021)
2-Hydroxyacetophenone (2-HAP) is an important building block for the production of a series of natural products and pharmaceuticals; however, there is no safe, efficient, and economical method for 2-HAP synthesis. Here, a one-pot enzymatic-chemical cascade route was designed for synthesizing 2-HAP based on retrosynthetic analysis. First, a spontaneous proton-transfer reaction was designed using a computational simulation that enabled 2-HAP synthesis from the isomer 2-hydroxy-2-phenylacetaldehyde. A route for 2-hydroxy-2-phenylacetaldehyde synthesis was then constructed by introducing the unnatural substrate glyoxylic acid into a C-C ligation reaction catalyzed by Candida tropicalis pyruvate decarboxylase. Assembly and optimization of this enzymatic-chemical cascade route resulted in a final yield of 92.7%. Furthermore, stereospecific carbonyl reductases were introduced to construct a synthetic application platform that enabled further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method of cascading spontaneous chemical and enzymatic reactions to synthesize chemicals offers insight into avenues for synthesizing other valuable chemicals.
HYPERVALENT IODINE OXIDATION OF 1-TRIMETHYLSILYLOXY,1-(2'-TRIMETHYLSILYLOXYPHENYL)ETHENE. SYNTHESIS OF 3-COUMARANONE AND 2,2'-DIHYDROXYACETOPHENONE
Moriarty, Robert M.,Prakash, Om,Duncan, Michael P.
, p. 1239 - 1246 (2007/10/02)
The oxidation of 1-trimethylsilyloxy,1-(2'-trimethylsilyloxyphenyl)ethene (6) with iodosobenzene, boron trifluoride etherate and water affords two major products, namely, 3-coumaranone (9, 31percent) and 2,2'-dihydroacetophenone (10, 25percent).Formation of 9 is explained by neihgboring group participation by the adjacent hydroxyl group.
