Diastereoselective synthesis of (2S*)-2-[(R*)-1H-indol-3-yl(phenyl)methyl]-2,3-dihydro-1H-inden-1-one

Tetrahedron Letters

Volumn 47, Issue 20, 2006, Pages 3479-3483

  Semenov, Boris B ^a   Novikov, Kirill A ^a   Lysenko, Konstantin A ^b   Kachala, Vadim V ^c  

^a MENDELEEV UNIVERSITY OF CHEMICAL TECHNOLOGY OF RUSSIA   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

GRAMINE; INDANONE DERIVATIVE; INDOLE DERIVATIVE; KETONE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 33646050323     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.158     Document Type: Article

References (19)

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3. 19
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6. Semenov, B. B. Ph.D. Dissertation, D. I. Mendeleev University of Chemical Technology, 2002.
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13. 21 +0.5 (c 2, DMSO).
14. 2 = 0.1532 and GOF = 0.938 for all independent reflections (R1 = 0.0581 was calculated against F for 1393 observed reflections with I > 2σ(I)). All calculations were performed using shelxtl plus 5.0. Crystallographic data (excluding structure factors) for the structures reported in this letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary no. 291553. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ UK (Fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk).
15. 2-[1H-Indol-3-yl(phenyl)methyl]-2,3-dihydro-1H-inden-1-one (0.089 g, 0.026 mmol) was added to a suspension of sodium borohydride (0.01 g, 0.026 mmol) in ethanol (10 ml) and the mixture was kept for two weeks at room temperature. The reaction mixture was poured into water and the resulting precipitate filtered off. Yield 80%. Mp 190 °C.
16. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), John Wiley & Sons, New York
17. *)-1H-indol-3-yl(phenyl)methyl]-2,3-dihydro-1H-inden-1-one was added. The mixture was stirred for 12 h at rt and poured into water; the resulting precipitate was filtered off. Yield 83%. Mp 210 °C.
18. Syntheses of organic compounds, Izd. Inostr. Lit. Moscow, 1956; Vol. 6, p 50 (in Russian).
19. Borisova V.N., Gordeev E.N., and Suvorov N.N. Khim. Geterotsikl. Soedin. (1967) 357-358