588-98-7Relevant academic research and scientific papers
SN2-Selective allylic substitution of chiral γ-aryl substituted allylic picolinates with alkynylcopper reagents
Wang, Qian,Kobayashi, Yuichi
, p. 5592 - 5595 (2010)
Substitution of γ-aryl secondary allylic picolinates with alkynyl copper reagents was studied. The copper reagent, prepared from TMSCCMgBr and CuBr·Me2S in 2:1, was subjected to substitution of the picolinate derived from (E)-3-phenyl-1-methyl-2-propenyl alcohol at 0 °C for 1 h in THF to produce a mixture of α-and γ-products and the alcohol in 67:20:13, while the reagent in 3 or 4:1 ratio gave the α-product with 90-91% selectivity. On the contrary, reaction in CH2Cl 2-THF (6-8:1) at 0 °C for 1 h furnished the α-product with 99% regioselectivity. The effect of CH2Cl2 was also demonstrated with eight more examples. Furthermore, 99% inversion was determined by transformation to the literature compound and by chiral HPLC.
Enzymatic cascades for the stereo-complementary epimerisation of in situ generated epoxy alcohols
Liu, Yu-Chang,Guo, Chao,Liu, Yan,Wang, Hai-Bo,Wu, Zhong-Liu
, p. 2562 - 2568 (2017/04/03)
The synthesis of optically pure secondary epoxy alcohols from racemic allylic alcohols using a single whole-cell biocatalyst of recombinant Escherichia coli coexpressing three oxidoreductases is described. The cascade involves the concurrent action of a styrene monooxygenase that catalyzes the formation of the chiral epoxy group, and two alcohol dehydrogenases that fulfil the epimerisation of the hydroxy group. Two sets of alcohol dehydrogenases were each applied to couple with styrene monooxygenase in order to realize the epimerisation in a stereo-complementary manner. Excellent enantio- and diastereo-selectivities were achieved for most of the 12 substrates.
