121133-16-2Relevant academic research and scientific papers
Enantiocomplementary Epoxidation Reactions Catalyzed by an Engineered Cofactor-Independent Non-natural Peroxygenase
Crotti, Michele,Kataja, Kim M.,Poelarends, Gerrit J.,Saravanan, Thangavelu,Xu, Guangcai
, p. 10374 - 10378 (2020/04/23)
Peroxygenases are heme-dependent enzymes that use peroxide-borne oxygen to catalyze a wide range of oxyfunctionalization reactions. Herein, we report the engineering of an unusual cofactor-independent peroxygenase based on a promiscuous tautomerase that accepts different hydroperoxides (t-BuOOH and H2O2) to accomplish enantiocomplementary epoxidations of various α,β-unsaturated aldehydes (citral and substituted cinnamaldehydes), providing access to both enantiomers of the corresponding α,β-epoxy-aldehydes. High conversions (up to 98 %), high enantioselectivity (up to 98 % ee), and good product yields (50–80 %) were achieved. The reactions likely proceed via a reactive enzyme-bound iminium ion intermediate, allowing tweaking of the enzyme's activity and selectivity by protein engineering. Our results underscore the potential of catalytic promiscuity for the engineering of new cofactor-independent oxidative enzymes.
Synthesis of arylnaphthalene lignan scaffold by gold-catalyzed intramolecular sequential electrophilic addition and benzannulation
Gudla, Vanajakshi,Balamurugan, Rengarajan
experimental part, p. 9919 - 9933 (2012/01/15)
An intramolecular approach to generate compounds containing an arylnaphthalene lignan scaffold in high yields is presented. It involves a sequential intramolecular electrophilic attack of carbonyl on arylalkyne followed by benzannulation catalyzed by gold salt. AuCl3 in combination with AgSbF6 works better to effect this transformation. Selected products have been converted into arylnaphthalene lactone natural products such as justicidin E, taiwanin C, and retrojusticidin B (Figure presented).
A NOVEL SYNTHESIS OF 2,3-EPOXY-3-ARYLPROPANOL VIA ARSONIUM SALT
Shi, Lilian,Wang, Weibo,Huang, Yao-Zeng
, p. 5295 - 5296 (2007/10/02)
In the presence of KOH(s), β-hydroxyethyltriphenylarsonium bromide 2 reacted directly with aromatic aldehydes at r.t. to give 2,3-epoxy-3-arylpropanol 3 in good yields under solid-liquid phase transfer condition.
