Diastereoselective ruthenium-Cp complexation of enantiopure arene compounds possessing stereogenic benzylic alcohol functionalities

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3667-3670

  Kamikawa, Ken ^a   Furusyo, Masaru ^b   Uno, Takahiro ^a   Sato, Yasuko ^a   Konoo, Atutoshi ^a   Bringmann, Gerhard ^c   Uemura, Motokazu ^a  

^a Osaka Prefecture University   (Japan)

^b SUMITOMO ELECTRIC INDUSTRIES LTD   (Japan)

^c UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001575410     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010197f     Document Type: Article

References (36)

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18. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with Cambridge Crystallographic Data Center as supplementary publication no. CCDC-165780. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax (+44) 1223-336-033; e-mail deposit@ccdc.cam.ac.uk).
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31. Geometry optimizations were carried out with B3LYP hybrid density functional theory on using 6-31G* (C, H, O) and LACVP (Ru) basis sets with the Gaussian 98 and Jaguar V3.5 suite of programs.
32. 3.
33. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with Cambridge Crystallographic Data Center as supplementary publication no. CCDC-165781.
34. -1.
35. A naphthyltetrahydroisoquinoline skeleton with a chiral center having sterically bulky substituants and specific nitrogen substitution could also fix the axial axis of δ-lactone-bridged biaryls by palladium-catalyzed cyclization: see ref 8c.
36. The δ-lactone ring opening of the ruthenium-uncomplexed biaryls 6 with NaOMe gave the diastereomeric mixture of axially atropisomeric biaryls (dr = 7:3 for 6a; 1:1 for 6b) on the basis of the axially equilibrated ratio of 6a and 6b. (19) Interestingly, a related ruthenium complex biaryl lactone ring could be opened only with O-nucleophues: see ref 7b. We are now investigating the reason for these different reactivities with hydride reduction between the related ruthenium complexes.