Asymmetric synthesis of hydroxylated pyrrolizidine, indolizidine, and (+)-α-conhydrine via ruthenium-catalyzed hydrogenation

Chirality

Volumn 12, Issue 5-6, 2000, Pages 408-410

  Guerreiro, Patricio ^a   Ratovelomanana Vidal, Virginie ^a   Genêt, Jean Pierre ^a,b  

^a Lab Synt Selective Organique P   (France)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

Alkaloids; Amino acids; Hydrogenation; Ruthenium

Indexed keywords

INDOLIZIDINE DERIVATIVE; PYRROLIZIDINE; RUTHENIUM;

ARTICLE; CHIRALITY; CONFORMATIONAL TRANSITION; DERIVATIZATION; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; HYDROXYLATION; PRIORITY JOURNAL;

EID: 0034116487     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(2000)12:5/6<408::AID-CHIR20>3.0.CO;2-G     Document Type: Article

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32. 33) (3.2 mg, 0.01 mmol) were placed in a 50-mL flask and 5 mL of anhydrous acetone were added dropwise. A methanolic solution of HBr (122 μL, 0.18 M) was added dropwise to the suspension. The reaction mixture was stirred at room temperature for about 30 min and a resulting yellow suspension was observed. The solvent was removed under vacuum. The yellow solid residue was used as catalyst for the hydrogenation reaction. Methanol or dichloromethane (2 mL) and appropriate substrate (1 mmol) were added and the reaction vessel were placed in a 500 mL stainless steel autoclave under argon. The autoclave was pressurized to the desired hydrogen pressure and the reaction was allowed to proceed until complete conversion.