42738-59-0Relevant academic research and scientific papers
Rhodium-catalyzed asymmetric addition of arylboronic acids to β-nitroolefins: Formal synthesis of (S)-SKF 38393
Huang, Kung-Chih,Gopula, Balraj,Kuo, Ting-Shen,Chiang, Chien-Wei,Wu, Ping-Yu,Henschke, Julian P.,Wu, Hsyueh-Liang
supporting information, p. 5730 - 5733 (2013/12/04)
An efficient enantioselective addition of an array of arylboronic acids to various β-nitrostyrenes catalyzed by a novel and reactive rhodium-diene catalyst (S/C up to 1000) was developed, providing β,β- diarylnitroethanes in good to high yields (62-99%) with excellent enantioselectivities (85-97% ee). The method was extended to 2-heteroarylnitroolefins and 2-alkylnitroolefins similarly providing the desired products with high enantioselectivities and yields. The usefulness of this method was demonstrated in the formal synthesis of the enantiomer of the dopamine receptor agonist and antagonist, SKF 38393.
Stereoisomeric probes for the D1 dopamine receptor: synthesis and characterization of R-(+) and S-(-) enantiomers of 3-allyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine and its 6-bromo analogue.
Neumeyer,Kula,Baldessarini,Baindur
, p. 1466 - 1471 (2007/10/02)
Substituted 1-phenyl-3-benzazepines (e.g., SKF 38393 and fenoldopam) exhibit stereoselectivity in moderately high-affinity binding to and partial agonist activation of D1 dopamine receptors. The 3-allyl (APB) and the 3-allyl-6-chloro (6-Cl-APB) analogues
Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine
Kaiser,Dandridge,Garvey,Hahn,Sarau,Setler,Bass,Clardy
, p. 697 - 703 (2007/10/02)
Resolution of the unique dopamine receptor agonist 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine (1) was achieved by a stereospecific multistep conversion of the readily separated enantiomers of its O,O,N-trimethylated diffractometric analysi
