108673-16-1Relevant academic research and scientific papers
Side chain hydroxylation of aromatic compounds by fungi. 1. Products and stereochemistry
Holland, Herbert L.,Bergen, Eleanor J.,Chenchaiah, P. Chinna,Khan, Shaheer H.,Munoz, Benito,et al.
, p. 502 - 507 (2007/10/02)
The fungus Mortierella isabellina can convert ethylbenzene and a number of para-substituted derivatives to the corresponding optically active 1-phenylethanols with enantiomeric excess between 5 and 40percent and chemical yields up to 45percent. 2-Ethylnaphthalene, 2-ethylthiophene, and n-propylbenzene were similarly converted, as were the bicyclic compounds indane and tetraline.In most cases, the R absolute configuration of product predominated.The fungi Cunninghamella echinulata var. elegans and Helminthosporium species are also capable of performing some of these transformations.M. isabellina and C. elegans also produce 2-phenylethanols as products in some cases.The highest enantiomeric excesses during benzylic hydroxylation were obtained with Helminthosporium and are attributable, at least in part, to further stereoselective oxidation of the alcohol.Cross induction experiments with M. isabellina indicate that the same enzyme may be responsible for the benzylic hydroxylation of ethylbenzene, 2-ethylthiophene, and 2-ethylnaphthalene.
