137628-46-7Relevant academic research and scientific papers
A green chemistry approach to a more efficient asymmetric catalyst: Solvent-free and highly concentrated alkyl additions to ketones
Jeon, Sang-Jin,Li, Hongmei,Walsh, Patrick J.
, p. 16416 - 16425 (2005)
There is a great demand for development of catalyst systems that are not only efficient and highly enantioselective but are also environmentally benign. Herein we report investigations into the catalytic asymmetric addition of alkyl and functionalized alk
trans-1,2-diaminocyclopentane-based catalyst for the asymmetric addition of alkyl-, aryl-, and vinyl groups to ketones
De Parrodi, Cecilia Anaya,Walsh, Patrick J.
, p. 2417 - 2420 (2007/10/03)
The catalytic asymmetric addition of ethyl-, phenyl-, and 1-hexenyl groups to ketones is reported. The new catalyst, generated from titanium wopropoxide and a bis(sulfonamide) diol ligand based on frans-1,2-diaminocyclopentane, gives good to excellent ena
Highly enantioselective addition of primary alkyl Grignard reagents to carbocyclic and heterocyclic arylketones in the presence of magnesium TADDOLate preparative and mechanistic aspects
Weber, Beat,Seebach, Dieter
, p. 6117 - 6128 (2007/10/02)
In the presence of equimolar amounts of the Mg alkoxide from α,α,α',α'-tetraphenyl-2,2-dimethyl-1,3-dioxolan-4,5-dimethanol (a TADDOL) primary Grignard reagents (Et, Pr, Bu, Oct, 3-butenyl) add to carbo- and heteroaromatic methyl ketones in THF at -100°C to give tertiary alcohols of enantiomeric excesses reaching values above 98%. The scope and limitation of the method are investigated. The reaction, which occurs in a vigorously stirred heterogeneous mixture, give best results in the absence of steric hindrance of the reacting centers; Grignard reagents made from alkyl bromides are superior to those obtained from chlorides; there is a perfect linear relationship between the ee of the TADDOL and of the product 2-phenyl-2-decanol; those tertiary alcohols of which the absolute configuration is known, are formed by nucleophilic attack from the Re face of the keto carbonyl groups. Three tentative mechanistic models for the stereochemical course of the reaction are discussed.
