194019-65-3

Upstream product

• 194019-61-9 3(R),4(S)-1-benzyl-N-tert-butoxycarbonyl-4-isopropenyl-N-(1-phenylethenyl)pyrrolidine-3-carboxamide 
• 194019-63-1 Toluene-4-sulfonic acid (3R,4R)-4-isopropyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylmethyl ester 
• 194019-52-8 3(R),4(S)-1-benzyl-4-isopropenyl-N-(1-phenylethenyl)pyrrolidine-3-carboxamide 
• 194019-62-0 ((3R,4S)-1-Benzyl-4-isopropenyl-pyrrolidin-3-yl)-methanol 
• 143140-13-0 (3S,5aR,8aS,8bR)-7-Benzyl-8b-methyl-3-phenyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one 
• 194019-50-6 1(R),4(R,S),5(S)-7-benzyl-4-hydroxy-4-methyl-3-(1-phenylethenyl)-3,7-diazabicyclo[3.3.0]octan-2-one 
• 194019-64-2 [(3R,4R)-4-Isopropyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile 

Relevant academic research and scientific papers

Asymmetric synthesis of 3,4-disubstituted pyrrolidines: 1,3-dipolar addition to chiral bicyclic lactams

The title compounds 1 are obtained in good yields from tricyclic lactams 2, which are derived from the asymmetric dipolar cycloaddition of azomethine ylides 4 to chiral bicyclic lactams 3.Thus, treatment of tricyclic adducts 14 or 17 with methyllithium gives N-substituted bicyclic hydroxylactams 16 or 18, respectively, as a consequence of abstraction of the kinetically acidic benzylic hydrogen followed by an anionic cycloreversion process.Alternatively, treatment of 14 or 48 with calcium metal in liquid ammonia gives N-unsubstituted bicyclic hydroxylactams 60 or 56 respectively.Through the intermediacy of these bicyclic hydroxylactams, illustrative examples of nonracemic monocyclic and bicyclic 3,4-disubstituted pyrrolidine 'building blocks' were synthesized bearing vicinal substituents which are amenable to facile chemical manipulation. - Keywords: 3,4-disubstituted pyrrolidine; asymmetric synthesis; 1,3-dipolar addition; bicyclic lactam; hydroxylactam