177948-63-9Relevant articles and documents
A new chiral synthesis of Wieland-Miescher ketone catalyzed by a combination of (S)-N- benzyl-N(2-pyrrolidinylmethyl)amine derivative and bronsted acid
Akahane, Yuichi,Inomata, Kohei,Endo, Yasuyuki
experimental part, p. 1065 - 1078 (2010/10/03)
New or known N-benzyl-N (2-pyrrolidinylmethyl)amine derivatives bearing a variety of substituents on the aromatic ring were easily prepared from N-Boc-proline or NBoc-prolinol. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail. During the examination, remarkable substitutional effects on the aromatic ring were observed. Development of a catalytic version of the reaction was successfully achieved by the use of N(9-anthracenyl)methyl-N(2-pyrrolidinyl-methyl)amine in the presence of dichloroacetic acid.