153186-41-5Relevant academic research and scientific papers
Polyfunctionalized pyrrolidines by stereoselective 1,3-dipolar cycloaddition of azomethine ylides to chiral enones
Galley,Liebscher,Patzel
, p. 5005 - 5010 (2007/10/03)
The cycloaddition reactions of chiral α,β-unsaturated ketones substituted by alkoxy or amino groups in the γ-position to azomethine ylides (obtained from glycine imines) were investigated in the presence of a base, LiBr and AgOAc. High regioselectivities were observed in most cases, resulting in the formation of a single diastereomer, particularly if a DBU/AgOAc catalyst system was employed. The influence of reaction conditions and olefin structure on the stereoselectivity of the reaction was investigated, and models rationalizing stereocontrol are proposed. In addition, an interesting deconjugation reaction of acetals derived from γ,δ-dihydroxy α,β-unsaturated enones or esters is described.
Synthesis of enantiomerically pure pyrrolidines by stereospecific cycloaddition of azomethine ylides with enones
Paetzel,Galley,Jones,Chrapkowsky
, p. 5707 - 5710 (2007/10/02)
Several (E)-α,β-unsaturated ketones (enones) 2 bearing a chiral alkoxy or amino substituent in γ-position react with azomethine ylides 3 (obtained from glycine imines) in the presence of DBU/ AgOAc giving enantiomerically pure pyrrolidine derivatives 4 in
