Enantioselective photocyclization of 2-arylthio-3-methylcyclohexen-1-ones to dihydrobenzothiophene derivatives in an inclusion crystal with an optically active host

Journal of the American Chemical Society

Volumn 118, Issue 45, 1996, Pages 11315-11316

  Toda, Fumio ^a   Miyamoto, Hisakazu ^a   Kikuchi, Shiro ^a   Kuroda, Reiko ^b   Nagami, Fuji ^b  

^a EHIME UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIOPHENE DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; CYCLIZATION; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029862763     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962481l     Document Type: Article

References (18)

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7. Toda, F.; Yagi, M.; Soda, S. J. Chem. Soc., Chem. Commun. 1987, 1413. Sekine, A.; Hori, K.; Ohashi, Y.; Yagi, M.; Toda, F. J. Am. Chem. Soc. 1989, 111, 697. Toda, F.; Tanaka, K. Supramol. Chem. 1994, 3, 87.
8. Toda, F.; Yagi, M.; Soda, S. J. Chem. Soc., Chem. Commun. 1987, 1413. Sekine, A.; Hori, K.; Ohashi, Y.; Yagi, M.; Toda, F. J. Am. Chem. Soc. 1989, 111, 697. Toda, F.; Tanaka, K. Supramol. Chem. 1994, 3, 87.
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10. Toda, F.; Tanaka, K.; Kakinoki, O.; Kawakami, T. J. Org. Chem. 1993, 58, 3783. Toda, F.; Miyamoto, H.; Kanemoto, K. J. Chem. Soc., Chem. Commun. 1995, 1719. Toda, F.; Miyamoto, H.; Kikuchi, S. J. Chem. Soc., Chem. Commun. 1995, 621.
11. Toda, F.; Tanaka, K.; Kakinoki, O.; Kawakami, T. J. Org. Chem. 1993, 58, 3783. Toda, F.; Miyamoto, H.; Kanemoto, K. J. Chem. Soc., Chem. Commun. 1995, 1719. Toda, F.; Miyamoto, H.; Kikuchi, S. J. Chem. Soc., Chem. Commun. 1995, 621.
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13. Irradiation was continued until no starting material was detected in IR.
14. The reaction product was separated by silica gel chromatography (ethyl acetate/n-hexane = 1:9). Enantiomeric excess of the sample was determined by HPLC on the chiral solid stationary phase Chiralpak AS, which is available from Daicel Chemical Industries, Ltd., Himeji, Japan.
15. 1H NMR spectra, they were assigned to be cis.
16. Crystal data for (-)-4a-5g: triclinic, colorless, a = 9.812(3) Å, b = 21.7121(3) Å, c = 9.477(2) Å, α = 91.26(1)°, β = 90.24(2)°, γ = 83.68-(2)°, space group P1, Z = 2, R = 0.069, and GOF = 2.66.
17. 1, Z = 8, R = 0.038, and GOF = 1.19.
18. CD spectra were measured on a Jasco J-720 spectropolarimeter: Kuroda, R. Ph.D. thesis, The University of Tokyo, 1975. Biscarini, R.; Franca, R.; Kuroda, R. Inorg. Chem. 1995, 34, 4618.