79120-95-9Relevant academic research and scientific papers
Cyanide-free enantioselective synthesis of nitriles: Synthetic proof of a biocatalytic concept and mechanistic insights
Metzner, Richard,Okazaki, Seiji,Asano, Yasuhisa,Gr?ger, Harald
, p. 3105 - 3109 (2015/02/18)
The first ( by definition ) cyanide-free enantioselective synthetic approach towards chiral α - and β -branched nitriles is reported. This process is based on a biocatalytic dehydration of racemic aldoximes by using an aldoxime dehydratase and proceeds with high conversion and excellent enantioselectivity (up to 98% ee) with water as the only side-product when starting from a racemic substrate with a high E/Z ratio. Thus, in combination with the facile generation of aldoximes through condensation of readily accessible aldehydes with hydroxylamine, this methodology offers an attractive and efficient path to chiral nitriles with excellent atom economy in aqueous solution. Furthermore, this study shows a surprising enzymatic dependency of the enantiopreference on the E or Z configuration of the aldoxime moiety. Notably, the whole stereochemical course of this enzymatic reaction has been rationalized by means of a computational study.
Conformational Analysis by Thermal Variation of Rotatory Power. Monosubstituted Cyclohexene Enantiomers
Lauricella, Robert,Kechayan, Josette,Bodot, Hubert
, p. 1577 - 1582 (2007/10/02)
The conformer rotatory powers of six 4-substituted cyclohexenes have been calculated by extension of the Brewster procedure and used to estimate the conformational free energy differences.The corresponding conformational rotivities are utilized to analyze
