167611-92-9Relevant academic research and scientific papers
Substrate Scope Evaluation of the Enantioselective Reduction of β-Alkyl-β-arylnitroalkenes by Old Yellow Enzymes 1-3 for Organic Synthesis Applications
Bertolotti, Mattia,Brenna, Elisabetta,Crotti, Michele,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Santangelo, Sara
, p. 577 - 583 (2016/02/23)
The substrate scope of the old yellow enzyme catalyzed reduction of β-alkyl-β-arylnitroalkenes is investigated. Compounds bearing either alkyl chains of increasing length at the carbon atom in position β to the nitro group or different substituents on the aromatic ring are prepared and submitted to bioreduction, to define the synthetic potential of this enantioselective reaction in the preparation of chiral fine chemicals. The versatility of the resulting nitroalkanes as chiral building blocks is shown by reducing the nitro group into a primary amine and by converting it into a carboxylic acid moiety by Meyer reaction. An "explosion" of chiral products can be observed by combining the highly enantioselective ene-reductase-mediated reduction of nitroalkenes with the chemical versatility of the nitro group.
Enantioselective Conjugate Addition of Primary Dialkylzinc Reagents to 2-Aryl- and 2-Heteroaryl-nitroolefins Mediated by Titanium-TADDOLates Preparation of Enantioenriched 2-Aryl-alkylamines
Schaefer, Harald,Seebach, Dieter
, p. 2305 - 2324 (2007/10/02)
The addition of dialkylzinc to nitroolefins is catalyzed by Lewis acids such as MgBr2, MgI2, and chlorotitanates.Using the (R,R)-Ti-TADDOLates the addition of diethyl-, dibutyl-, and dioctyl zinc to 2-aryl-nitroethenes is shown to be enantioselective with
