504432-48-8Relevant academic research and scientific papers
Enzymatic synthesis of optically active lactones via asymmetric bioreduction using ene-reductases from the old yellow enzyme family
Turrini, Nikolaus G.,Hall, Mélanie,Faber, Kurt
supporting information, p. 1861 - 1871 (2015/06/02)
In contrast to the widely studied asymmetric bioreduction of α,β-unsaturated carboxylic acid esters catalyzed by ene-reductases, the reaction applied to lactones remains unexplored. A broad set of ene-reductases was found to reduce various α-, β- and γ-substituted α,β-unsaturated butyrolactones to yield the corresponding saturated non-racemic lactones. Substitution patterns greatly influenced activities and stereoselectivities and lactone products were obtained in moderate to excellent yields; importantly, enzyme-based stereocontrol allowed access to both enantiomers in up to >99% ee. Chiral recognition of a distant γ-center led to kinetic resolution with remarkable enantioselectivities (E values up to 49). An unprecedented case of dynamic kinetic resolution was observed with 3-methyl-5-phenylfuran-2(5H)-one, whereby spontaneous racemization of the substrate furnished the product in up to 73% conversion and >99% ee and 96% de.
Copper(I) chloride mediated cyclization of optically active 2,3-allenoic acids or 1:1 salts of optically active 2,3-allenoic acids with chiral amines
Ma, Shengming,Yu, Zhanqian
, p. 3711 - 3714 (2008/09/16)
Copper(I) chloride mediated cyclization of optically active 2,3-allenoic acids or 1:1 salts of optically active 2,3-allenoic acids with chiral amines was developed. The reaction of optically active 2,3-allenoic acids in methanol requires only a catalytic
