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Volumn 11, Issue 4, 2007, Pages 726-730

Development of a large-scale stereoselective process for (1 R,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride

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EID: 34547891014     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op7000589     Document Type: Article
Times cited : (35)

References (44)
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    • For a review on applications of tert-butylsulfinamide see
    • (a) For a review on applications of tert-butylsulfinamide see: Ellman, J. A.; Owens, T., D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
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    • For a recent general review on the synthesis and applications of sulfinamides see: a
    • (b) For a recent general review on the synthesis and applications of sulfinamides see: (a) Senanayake, C. H.; Krishnamurthy, D.; Lu, Z-H.; Han, Z.; Gallou, I. Aldrichimica Acta 2005, 38, 93.
    • (2005) Aldrichimica Acta , vol.38 , pp. 93
    • Senanayake, C.H.1    Krishnamurthy, D.2    Lu, Z.-H.3    Han, Z.4    Gallou, I.5
  • 19
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    • Hydrogenation of various imine derivatives derived from (4S)-3 provided predominantly cis product.
    • Hydrogenation of various imine derivatives derived from (4S)-3 provided predominantly cis product.
  • 20
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    • For reviews on the chemistry of sulfinimines see: a
    • For reviews on the chemistry of sulfinimines see: (a) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
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    • Davis, F.A.1    Zhou, P.2    Chen, B.-C.3
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    • Synthesis and Reactions of Sufinimines
    • Rayner, C. M, Ed, JAI: Greenwich, Connecticut
    • (c) Zhou, P.; Chen, B.-C.; Davis, F. A. Synthesis and Reactions of Sufinimines. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI: Greenwich, Connecticut, 2000; Vol. 2, pp 249-282.
    • (2000) Advances in Sulfur Chemistry , vol.2 , pp. 249-282
    • Zhou, P.1    Chen, B.-C.2    Davis, F.A.3
  • 27
    • 34547908295 scopus 로고    scopus 로고
    • s,4S)-5, 29.6 min; 7, 24.8 min; 1, 11.5 min.
    • s,4S)-5, 29.6 min; 7, 24.8 min; 1, 11.5 min.
  • 33
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    • 2 see: Xiao, X.; Wang, H.; Huang, G.; Yang, J.; Bian, X.; Qin, Y. Org. Lett. 2006, 8, 139.
    • 2 see: Xiao, X.; Wang, H.; Huang, G.; Yang, J.; Bian, X.; Qin, Y. Org. Lett. 2006, 8, 139.
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    • For the asymmetric reduction of tert-butylsulfinyl imines see: a
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    • Kochi, T.1    Tang, T.P.2    Ellman, J.A.3
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    • 3b,4 = 8.4 Hz), 3.44 (ddd, 1H, J = 4.0, 7.6, 13.2 Hz), 2.89 (ddd, 1H, J = 4.4, 9.6, 13.2 Hz), 2.42 (s, 3H), 2.32 (m, 1H,), 2.17 (m, 1H).
    • 3b,4 = 8.4 Hz), 3.44 (ddd, 1H, J = 4.0, 7.6, 13.2 Hz), 2.89 (ddd, 1H, J = 4.4, 9.6, 13.2 Hz), 2.42 (s, 3H), 2.32 (m, 1H,), 2.17 (m, 1H).
  • 38
    • 34547898557 scopus 로고    scopus 로고
    • (R)-p-Toluene sulfinamide is listed in the Aldrich 2006 catalogue at 0.5g/ $59.40, whereas the (S)-isomer is listed at 5.0g/$126.50.
    • (R)-p-Toluene sulfinamide is listed in the Aldrich 2006 catalogue at 0.5g/ $59.40, whereas the (S)-isomer is listed at 5.0g/$126.50.
  • 41
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    • 16 when sodium borohydride was used as reducing agent in methanol as compared to more sterically demanding 9-BBN in THF. Also, sodium borohydride in THF at 0°C gave 95% conversion and reverse selectivity of 85/15 trans/cis. However, L-Selectride in THF at 0 °C gave > 99% conversion and 1/99 ratio of trans/cis.
    • 16 when sodium borohydride was used as reducing agent in methanol as compared to more sterically demanding 9-BBN in THF. Also, sodium borohydride in THF at 0°C gave 95% conversion and reverse selectivity of 85/15 trans/cis. However, L-Selectride in THF at 0 °C gave > 99% conversion and 1/99 ratio of trans/cis.
  • 44
    • 34547889273 scopus 로고    scopus 로고
    • 2O, 95:5:0.05:0.01; flow rate of 0.8 mL/minute; ambient temperature; 220 nm wavelength. Approximate retention times for (1R,4S)-1, 39 min; for (1S,4S)-1, 36 min. In addition, this verified that no epimerization of the 45 center occurred during processing.
    • 2O, 95:5:0.05:0.01; flow rate of 0.8 mL/minute; ambient temperature; 220 nm wavelength. Approximate retention times for (1R,4S)-1, 39 min; for (1S,4S)-1, 36 min. In addition, this verified that no epimerization of the 45 center occurred during processing.


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