Copper ion-catalyzed regioselective introduction of active methylene groups into the γ-position of piperidine skeleton and its application to the synthesis of (-)-cincholoiponic acid

Tetrahedron Letters

Volumn 47, Issue 31, 2006, Pages 5485-5488

  Minato, Daishirou ^a   Imai, Mieko ^a   Kanda, Yasuhisa ^a   Onomura, Osamu ^a   Matsumura, Yoshihiro ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Asymmetric; Copper; Nucleophilic substitution; Piperidine; Regioselective

Indexed keywords

CARBENE; CINCHOLOIPONIC ACID; COPPER ION; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY;

EID: 33745235056     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.158     Document Type: Article

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47. Table 1 shows only the yields of major products.
48. 4. The resulting solution was concentrated in vacuo. The residue was chromatographed on silica gel (hexane/AcOEt = 5/1) to afford 9bq* (88% yield, diastereomer ratio = 56 (43% ee): 44 (44% ee)).
49. 29 -8.3 (c 1.0, MeOH)].