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Volumn 13, Issue 6, 2009, Pages 1161-1168

Practical enantioselective synthesis of a 3-aryl-3-trifluoromethyl-2- aminopropanol derivative

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EID: 72449146232     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900216v     Document Type: Article
Times cited : (30)

References (33)
  • 22
    • 72449130199 scopus 로고    scopus 로고
    • note
    • Interestingly, examination of experimental details in various reports of HWE olefination of phenyl trifluoromethyl ketone in THF or toluene using NaH as a base might suggest an opposite hold-time/selectivity relationship.
  • 23
    • 72449133548 scopus 로고    scopus 로고
    • note
    • Walphos 8-1: (R)-1-[(R)-2-(22 -dicyclohexylphosphinophenyl-)ferrocenyl] ethyldi(bis-(3,5-trifluoromethyl)phenyl)phosphine, available from Solvias, SL-W008-1; nbd: norbornadiene.
  • 26
    • 20744436699 scopus 로고    scopus 로고
    • Anti-diastereomer formation with up to 80% de was reported for a similar substrate with electron-rich aryl substituent and BnBr as an electrophile; 62% de and low conversion was reported for Nelectrophile. Tamura, K.; Yamazaki, T.; Kitazume, T.; Kubota, T. J. Fluorine Chem. 2005, 126, 918.
    • (2005) J. Fluorine Chem. , vol.126 , pp. 918
    • Tamura, K.1    Yamazaki, T.2    Kitazume, T.3    Kubota, T.4
  • 27
    • 72449181575 scopus 로고    scopus 로고
    • Production of pure chiral amino alcohol intermediates, derivatives thereof, and uses thereof
    • U.S. Patent Publ. Appl. US 2007/249869, 2007
    • (a) Sellstedt, J.; Cheal, G.; Noureldin, R.; Chan, A.W.-Y.; Raveendranath, P.; Caggiano, T. J. Production of Pure Chiral Amino Alcohol Intermediates, Derivatives Thereof, and Uses Thereof. U.S. Patent Publ. Appl. US 2007/249869, 2007; Chem. Abstr. 2007, 147, 486150.
    • (2007) Chem. Abstr. , vol.147 , pp. 486150
    • Sellstedt, J.1    Cheal, G.2    Noureldin, R.3    Chan, A.W.-Y.4    Raveendranath, P.5    Caggiano, T.J.6
  • 29
    • 72449164193 scopus 로고    scopus 로고
    • note
    • Once again, the (R)-enantiomer of benzyloxazolidinone chiral auxiliary needed for introduction of (S)-stereocenter at the β-position that way would not generate the required diastereomer after α-azidation.
  • 31
    • 72449161836 scopus 로고    scopus 로고
    • note
    • In a typical run, 4-5 HPLC area % of 18 was formed, with 2.1% remaining after crystallization.
  • 33
    • 43949160561 scopus 로고
    • For triisopropylsulfonyl azide stability data, see: Tuma, L. D. Thermochim. Acta 1994, 243, 161.
    • (1994) Thermochim. Acta , vol.243 , pp. 161
    • Tuma, L.D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.