1370522-27-2Relevant academic research and scientific papers
Enantioselective organocatalytic α-alkylation of ketones by S N1-type reaction of alcohols
Trifonidou, Maria,Kokotos, Christoforos G.
, p. 1563 - 1568 (2012/04/23)
The enantioselective α-alkylation reaction of cyclic ketones is described. Our catalyst, based on a "privileged" pyrrolidine ring bearing a chiral thioxotetrahydropyrimidinone ring, is a highly reactive catalyst for cyclic ketones. When this catalyst was coupled with in situ generated carbocations derived from alcohols, the corresponding α-alkylated adducts were obtained in moderate to quantitative yields and low to high enantioselectivities (up to 80% ee). The catalyst loading can be efficiently reduced to 10%, which is the lowest value reported in the literature for such an organocatalytic transformation.
