메뉴 건너뛰기




Volumn 72, Issue 13, 2007, Pages 4864-4871

A novel crystallization-induced diastereomeric transformation based on a reversible carbon-sulfur bond formation. Application to the synthesis of a γ-secretase inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL BONDS; CRYSTALLIZATION; ENZYME INHIBITION; SYNTHESIS (CHEMICAL);

EID: 34347216384     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0705925     Document Type: Article
Times cited : (7)

References (93)
  • 1
    • 5744225747 scopus 로고    scopus 로고
    • Pertinent reviews of Alzheimer's disease, the β-amyloid hypothesis and potential disease-modifying therapies can be found in the following references: (a) Larner, A
    • Pertinent reviews of Alzheimer's disease, the β-amyloid hypothesis and potential disease-modifying therapies can be found in the following references: (a) Larner, A. Expert Opin. Ther. Pat. 2004, 14, 1403.
    • (2004) Expert Opin. Ther. Pat , vol.14 , pp. 1403
  • 15
    • 2942538366 scopus 로고    scopus 로고
    • Selected articles: (a) Prasad, C. V. C.; Vig, S.; Smith, D. W.; Gao, Q.; Polson, C. T.; Corsa, J. A.; Guss, V. L.; Loo, A.; Barren, D. M.; Zheng, M.; Felsenstein, K. M.; Roberts, S. B. Bioorg. Med. Chem. Lett. 2004, 14, 3535.
    • Selected articles: (a) Prasad, C. V. C.; Vig, S.; Smith, D. W.; Gao, Q.; Polson, C. T.; Corsa, J. A.; Guss, V. L.; Loo, A.; Barren, D. M.; Zheng, M.; Felsenstein, K. M.; Roberts, S. B. Bioorg. Med. Chem. Lett. 2004, 14, 3535.
  • 23
    • 0014230664 scopus 로고    scopus 로고
    • N1 type additions of thiols to cyclohexyl benzylic positions are rare but have been noted; see: (a) Koenig, W.; Geiger, R.; Siedel, W. Chem. Ber. 1968, 101, 681-693.
    • N1 type additions of thiols to cyclohexyl benzylic positions are rare but have been noted; see: (a) Koenig, W.; Geiger, R.; Siedel, W. Chem. Ber. 1968, 101, 681-693.
  • 24
    • 0347510890 scopus 로고    scopus 로고
    • Additions to simple tertiary benzylic moieties are more prevalent; see: b
    • Additions to simple tertiary benzylic moieties are more prevalent; see: (b) Nishino, T.; Nishiyama, Y.; Sonoda, N. Chem. Lett. 2003, 32, 918.
    • (2003) Chem. Lett , vol.32 , pp. 918
    • Nishino, T.1    Nishiyama, Y.2    Sonoda, N.3
  • 27
    • 0027976883 scopus 로고    scopus 로고
    • By analogy with the preferred axial attack of sterically unencumbered nucleophiles on conformationally-locked, cyclohexyl centers. See (a) Greeves, N, Lyford, L, Pease, E. J. Tetrahedron Lett. 1994, 35, 285
    • By analogy with the preferred axial attack of sterically unencumbered nucleophiles on conformationally-locked, cyclohexyl centers. See (a) Greeves, N.; Lyford, L.; Pease, E. J. Tetrahedron Lett. 1994, 35, 285.
  • 36
    • 0034684515 scopus 로고    scopus 로고
    • Tertiary benzylic thiols are labile under acidic conditions: (a) Horton, J. R.; Stamp, L. M.; Routledge, A. Tetrahedron Lett. 2000, 41, 9181.
    • Tertiary benzylic thiols are labile under acidic conditions: (a) Horton, J. R.; Stamp, L. M.; Routledge, A. Tetrahedron Lett. 2000, 41, 9181.
  • 38
    • 33746874836 scopus 로고    scopus 로고
    • These processes are sometimes, less accurately, described as crystallization-induced dynamic resolutions. For a review, see
    • These processes are sometimes, less accurately, described as crystallization-induced dynamic resolutions. For a review, see Brands, K. J. M.; Davies, A. J. Chem. Rev. 2006, 106, 2711.
    • (2006) Chem. Rev , vol.106 , pp. 2711
    • Brands, K.J.M.1    Davies, A.J.2
  • 53
    • 0035808866 scopus 로고    scopus 로고
    • Also known as 'self-controlled' resolutions. For the evolution of this term, see
    • Also known as 'self-controlled' resolutions. For the evolution of this term, see: Kanomata, N.; Yoshiharu, O. Tetrahedron Lett. 2001, 42, 1045.
    • (2001) Tetrahedron Lett , vol.42 , pp. 1045
    • Kanomata, N.1    Yoshiharu, O.2
  • 62
    • 2442534663 scopus 로고    scopus 로고
    • The analogous reduction of phenol to cyclohexanone is a known process. For some recent articles, see a
    • The analogous reduction of phenol to cyclohexanone is a known process. For some recent articles, see (a) Ohde, H.; Ohde, M.; Wai, C. M. Chem. Commun. 2004, 8, 930.
    • (2004) Chem. Commun , vol.8 , pp. 930
    • Ohde, H.1    Ohde, M.2    Wai, C.M.3
  • 69
    • 85137635843 scopus 로고    scopus 로고
    • The chemoselective addition of an allyl organometallic reagent to a ketone in the presence of an acid moiety has been reported in Kumar, S, Kaur, P, Chimni, S. S. Synlett 2002, 573 and references therein
    • The chemoselective addition of an allyl organometallic reagent to a ketone in the presence of an acid moiety has been reported in Kumar, S.; Kaur, P.; Chimni, S. S. Synlett 2002, 573 and references therein.
  • 71
    • 34347244058 scopus 로고    scopus 로고
    • 6-DMSO) showed it to be stable at ambient temperature for at least 16 h.
    • 6-DMSO) showed it to be stable at ambient temperature for at least 16 h.
  • 72
    • 34347268291 scopus 로고    scopus 로고
    • Residual ketoacid was always seen in the crude reaction mixtures after work-up
    • Residual ketoacid was always seen in the crude reaction mixtures after work-up.
  • 73
    • 2342572295 scopus 로고    scopus 로고
    • Selected references on 4-fluorobenzyne: (a) Liu, H.; Zhang, X.; Wang, C.; Guo, W.; Wu, Y.; Yang, S. J. Phys. Chem. A 2004, 108, 3356.
    • Selected references on 4-fluorobenzyne: (a) Liu, H.; Zhang, X.; Wang, C.; Guo, W.; Wu, Y.; Yang, S. J. Phys. Chem. A 2004, 108, 3356.
  • 77
    • 3943099915 scopus 로고    scopus 로고
    • For a detailed study on the stability of 2-lithio-1,4-difluorobenzene and the corresponding Grignard reagent, see Scott, J. P.; Brewer, S. E.; Davies, A. J.; Brands, K. M. J. Synlett 2004, 9, 1646.
    • For a detailed study on the stability of 2-lithio-1,4-difluorobenzene and the corresponding Grignard reagent, see Scott, J. P.; Brewer, S. E.; Davies, A. J.; Brands, K. M. J. Synlett 2004, 9, 1646.
  • 78
    • 7044239411 scopus 로고    scopus 로고
    • The physical form of the cerium chloride used in the transmetalation step is crucial in ensuring high yields. For a detailed investigation, see Conlon, D. A, Kumke, D, Moeder, C, Hardiman, M, Hutson, G, Sailer, L. Adv. Synth. Catal. 2004, 346, 1307
    • The physical form of the cerium chloride used in the transmetalation step is crucial in ensuring high yields. For a detailed investigation, see Conlon, D. A.; Kumke, D.; Moeder, C.; Hardiman, M.; Hutson, G.; Sailer, L. Adv. Synth. Catal. 2004, 346, 1307.
  • 79
    • 0003942864 scopus 로고
    • The increasing proportion of equatorial vs axial attack on cyclohexananones, with increasing steric nucleophilic bulk has been noted, see a, Wiley-Interscience: New York
    • The increasing proportion of equatorial vs axial attack on cyclohexananones, with increasing steric nucleophilic bulk has been noted, see (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; pp 735-736, 880-887.
    • (1994) Stereochemistry of Organic Compounds
    • Eliel, E.L.1    Wilen, S.H.2    Mander, L.N.3
  • 84
    • 34347219972 scopus 로고    scopus 로고
    • Based on survey of potential commercial suppliers
    • Based on survey of potential commercial suppliers.
  • 85
    • 34347216567 scopus 로고    scopus 로고
    • 2-Lithio-1,4-difluorobenzene can also be prepared by halogen-metal exchange using n-BuLi according to the procedure of Butler, I. R.; Lindsell, W. E.; Preston. P. N. J. Chem. Res. Synop. 1981, 7, 185.
    • 2-Lithio-1,4-difluorobenzene can also be prepared by halogen-metal exchange using n-BuLi according to the procedure of Butler, I. R.; Lindsell, W. E.; Preston. P. N. J. Chem. Res. Synop. 1981, 7, 185.
  • 86
    • 0000775931 scopus 로고    scopus 로고
    • The aryllithium reagent is most likely complexed with TMEDA in our reaction. Axial addition predominates in the addition of phenyllithium to 4-tert-butylcyclohexanone, see Ashby, E. C.; Noding, S. R. J. Org. Chem. 1979, 44, 4371.
    • The aryllithium reagent is most likely complexed with TMEDA in our reaction. Axial addition predominates in the addition of phenyllithium to 4-tert-butylcyclohexanone, see Ashby, E. C.; Noding, S. R. J. Org. Chem. 1979, 44, 4371.
  • 87
    • 33845552223 scopus 로고    scopus 로고
    • The following acid catalysts were screened in the reaction of 4-chlorothiophenol with 4a and 4b in dichloromethane: Sc(OTf) 3, Ti(OEt)4, BF3·Et2O, Et2AlCl, Zn(OTf)2, ZnI2, SnCl2, SnCl4, TiCl4, InCl2, InCl3, LiClO4, B(OMe)3, BEt3, EtAlCl2, MeAlCl2, AlCl3, AlBr3, MeSO3H, CF3-SO3H, CF3SO2)2NH. Phenylthio ethers have been prepared previously from tertiary alcohols using ZnI2 as the Lewis acid, see Guindon, Y, Frenette, R, Fortin, R, Rokach, J. J. Org. Chem. 1983, 48, 1357
    • 2 as the Lewis acid, see Guindon, Y.; Frenette, R.; Fortin, R.; Rokach, J. J. Org. Chem. 1983, 48, 1357.
  • 88
    • 34347251766 scopus 로고    scopus 로고
    • A total of 47 solvents and solvent combinations were screened
    • A total of 47 solvents and solvent combinations were screened.
  • 89
    • 0004018410 scopus 로고
    • A solvent quoted as possessing a higher polarity than water, see, VCH (UK) Ltd, Cambridge
    • A solvent quoted as possessing a higher polarity than water, see Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH (UK) Ltd.: Cambridge, 1990; p 366.
    • (1990) Solvents and Solvent Effects in Organic Chemistry , pp. 366
    • Reichardt, C.1
  • 90
    • 34347248259 scopus 로고    scopus 로고
    • This solvent was chosen because it is miscible with 1,1,1,3,3,3- hexafluoro-2-propanol, without enhancing the solubility of 8 and 9
    • This solvent was chosen because it is miscible with 1,1,1,3,3,3- hexafluoro-2-propanol, without enhancing the solubility of 8 and 9.
  • 91
    • 0037048606 scopus 로고    scopus 로고
    • Thioethers have been prepared using dodecylbenzenesulfonic acid-catalyzed dehydration of alcohols, see
    • Thioethers have been prepared using dodecylbenzenesulfonic acid-catalyzed dehydration of alcohols, see Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 11971
    • Manabe, K.1    Iimura, S.2    Sun, X.-M.3    Kobayashi, S.4
  • 92
    • 34347269032 scopus 로고    scopus 로고
    • The structures of 8 and 9 were confirmed by single-crystal X-ray crystallography. See Supporting Information for details.
    • The structures of 8 and 9 were confirmed by single-crystal X-ray crystallography. See Supporting Information for details.
  • 93
    • 0001074604 scopus 로고
    • Trost, B. M, Fleming, I, Ley, S. V, Eds, Pergamon Press: Oxford, and references therein
    • Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Ley, S. V., Eds.; Pergamon Press: Oxford, 1993; vol. 7, p 766 and references therein.
    • (1993) Comprehensive Organic Synthesis , vol.7 , pp. 766


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.