A novel enantioselective synthesis of the key intermediate of (-)-huperzine A employing asymmetric palladium-catalyzed bicycloannulation

Tetrahedron Asymmetry

Volumn 8, Issue 6, 1997, Pages 829-832

  Kaneko, Satoru ^a   Yoshino, Toshiharu ^a   Katoh, Tadashi ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HUPERZINE A;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030989410     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00048-7     Document Type: Article

References (22)

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19. Using other chiral phosphine ligands, the representative ees observed for the reactions in the presence of 1,1,3,3-tetramethylguanidine (TMG) in 1,4-dioxane at room temperature were as follows: (A)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (12% ee), (2S,4S)-1-terf-butoxycarbony 1-4-diphenylphosphino-2-diphenylphosphinomethyl pyrrolidine (24% ee), (R.R)-1,2-ethanediylbis[(2-methoxyphenyl)phenyl-phosphine] (12% ee).
20. CHIRALCEL OD-H (DAICEL CHEMICAL INDUSTRIES, LTD) was used. Eluent (hexane:2-propanol=20:1) was flown by 0.5 ml/min and the products were detected by UV (254 nm).
21. 7a,b
22. 7b