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Volumn 10, Issue 13, 2008, Pages 2725-2728

An improved lanthanum catalyst system for asymmetric amination: Toward a practical asymmetric synthesis of AS-3201 (ranirestat)

Author keywords

[No Author keywords available]

Indexed keywords

LANTHANUM; PYRAZINE DERIVATIVE; SPIRO COMPOUND; SX 3030;

EID: 51649090667     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8008446     Document Type: Article
Times cited : (65)

References (50)
  • 30
    • 59949102927 scopus 로고    scopus 로고
    • Cu-Box, La-PyBox, urea-type organocatalyst, and cinchona alkaloids were screened in catalytic asymmetric amination of 1. The observed enantioselectivities were less than 30% ee. See also ref 6.
    • Cu-Box, La-PyBox, urea-type organocatalyst, and cinchona alkaloids were screened in catalytic asymmetric amination of 1. The observed enantioselectivities were less than 30% ee. See also ref 6.
  • 31
    • 33748413162 scopus 로고    scopus 로고
    • For recent selected examples of small peptide-based asymmetric catalysis, see:a
    • For recent selected examples of small peptide-based asymmetric catalysis, see:(a) Zhao, Y.; Rodrigo, J.; Hoveyda, A. H.; Snapper, M. C. Nature 2006, 443, 67.
    • (2006) Nature , vol.443 , pp. 67
    • Zhao, Y.1    Rodrigo, J.2    Hoveyda, A.H.3    Snapper, M.C.4
  • 35
    • 59949101452 scopus 로고    scopus 로고
    • Sigma-Aldrich Handbook of Fine Chemicals 2007-2008.
    • Sigma-Aldrich Handbook of Fine Chemicals 2007-2008.
  • 36
    • 59949086932 scopus 로고    scopus 로고
    • Bulk purchase may lower the cost
    • Bulk purchase may lower the cost.
  • 37
    • 0037433497 scopus 로고    scopus 로고
    • For recent selected examples for the use of lanthanide nitrates for asymmetric catalysis, see:a
    • For recent selected examples for the use of lanthanide nitrates for asymmetric catalysis, see:(a) Hamada, T.; Manabe, K.; Ishikawa, S.; Nagayama, S.; Shiro, M.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 2989.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 2989
    • Hamada, T.1    Manabe, K.2    Ishikawa, S.3    Nagayama, S.4    Shiro, M.5    Kobayashi, S.6
  • 39
    • 0038412630 scopus 로고    scopus 로고
    • Lanthanide niterates exhibit much less catalytic efficiency compared with corresponding triflates. RAJIV11For example, see: (c) Kano, S; Nakano, H; Kojima, M; Baba, N; Nakajima, K
    • Lanthanide niterates exhibit much less catalytic efficiency compared with corresponding triflates. RAJIV11For example, see: (c) Kano, S; Nakano, H; Kojima, M; Baba, N; Nakajima, K. Inorg. Chim. Acta 2003, 349, 6.
    • (2003) Inorg. Chim. Acta , vol.349 , pp. 6
  • 40
    • 0001045470 scopus 로고    scopus 로고
    • For selected examples of rare earth metal asymmetric catalyst showing enhanced stereoselectivity in the presence of amine, see:(a) Kobayashi, S, Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083
    • For selected examples of rare earth metal asymmetric catalyst showing enhanced stereoselectivity in the presence of amine, see:(a) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083.
  • 46
    • 59949104641 scopus 로고    scopus 로고
    • 2O was calculated as x = 4.
    • 2O was calculated as x = 4.
  • 47
    • 59949091636 scopus 로고    scopus 로고
    • A 25 g portion of di-tert-butyl azodicarboxylate was added five times during the first 5 min of the reaction. An additional 13.5 g was added 10 min after the last addition. The reaction was exothermic, and the reaction temperature varied from -5 to +8°C occasionally. The observed enantioselectivity was comparable to that obtained in small scale reactions likely because the enantioselectivity of the present amination is relatively insensitive to the reaction temperature.
    • A 25 g portion of di-tert-butyl azodicarboxylate was added five times during the first 5 min of the reaction. An additional 13.5 g was added 10 min after the last addition. The reaction was exothermic, and the reaction temperature varied from -5 to +8°C occasionally. The observed enantioselectivity was comparable to that obtained in small scale reactions likely because the enantioselectivity of the present amination is relatively insensitive to the reaction temperature.
  • 48
    • 59949084460 scopus 로고    scopus 로고
    • Enantiomeric excess of 5 was determined after mono-Boc protection. See the Supporting Information for details.
    • Enantiomeric excess of 5 was determined after mono-Boc protection. See the Supporting Information for details.
  • 50
    • 59949084946 scopus 로고    scopus 로고
    • The Clarke number of lanthanum is 0.0018, almost equally abundant as zinc (0.004) or boron (0.001).
    • The Clarke number of lanthanum is 0.0018, almost equally abundant as zinc (0.004) or boron (0.001).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.