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Volumn 72, Issue 4, 2007, Pages 1514-1517

Unexpected 1,5-dilithiation of chiral o-TMS blocked (dimethylamino) phenylmethylferrocene: An alternative approach to chiral ferrocenyl 1,5-diphosphanes

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOMERS; DILITHIATION; ENANTIOMERS; GRIGNARD REAGENT;

EID: 33846958797     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062210l     Document Type: Article
Times cited : (16)

References (21)
  • 12
    • 0042238447 scopus 로고    scopus 로고
    • For a review of ferrocenyl phosphines in asymmetric synthesis, see
    • For a review of ferrocenyl phosphines in asymmetric synthesis, see: Colacot, T. J. Chem. Rev. 2003, 103, 3101-3118.
    • (2003) Chem. Rev , vol.103 , pp. 3101-3118
    • Colacot, T.J.1
  • 13
    • 33847006779 scopus 로고    scopus 로고
    • 2Br gave 93% of the corresponding (R,Sp)-mono bromide together with 7% of the 1,5-dibromide.
    • 2Br gave 93% of the corresponding (R,Sp)-mono bromide together with 7% of the 1,5-dibromide.
  • 14
    • 0343435902 scopus 로고    scopus 로고
    • We are surprised at the inversion of the stereochemistry because it has been reported that the displacement of a dimethylamino group in the chiral ferrocenyl amine by the methoxide ion proceeds with retention. The mechanism of the inversive dimethylaminophenylmethyl case may be different from that of the retentive dimethylaminoethyl case, a Marquarding, D, Klusacek, H, Gokel, G, Hoffmann, P, Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389-5393
    • We are surprised at the inversion of the stereochemistry because it has been reported that the displacement of a dimethylamino group in the chiral ferrocenyl amine by the methoxide ion proceeds with retention. The mechanism of the inversive dimethylaminophenylmethyl case may be different from that of the retentive dimethylaminoethyl case. (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389-5393.
  • 17
    • 33746410089 scopus 로고    scopus 로고
    • The preparative method for the (S,Sp)-methoxy Taniaphos without separation has been reported recently while we were preparing this paper. Chen, W.; Roberts, S. M.; Whittall, J.; Steiner, A. Chem. Commun. 2006, 2916-2918.
    • The preparative method for the (S,Sp)-methoxy Taniaphos without separation has been reported recently while we were preparing this paper. Chen, W.; Roberts, S. M.; Whittall, J.; Steiner, A. Chem. Commun. 2006, 2916-2918.
  • 18
    • 22744436808 scopus 로고    scopus 로고
    • For a review for the copper-catalyzed asymmetric allylic substitution, see: a
    • For a review for the copper-catalyzed asymmetric allylic substitution, see: (a) Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 4435-4439.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 4435-4439
    • Yorimitsu, H.1    Oshima, K.2
  • 20
    • 0002634798 scopus 로고    scopus 로고
    • For a review of asymmetric hydrogenation, see:, 2nd ed, Ojima, I, Ed, Wiley-VCH: New York
    • For a review of asymmetric hydrogenation, see: Ohkuma, T.; Kitamura, M.; Noyori, R. Asymmetric Hydrogenation, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110.
    • (2000) Asymmetric Hydrogenation , pp. 1-110
    • Ohkuma, T.1    Kitamura, M.2    Noyori, R.3
  • 21
    • 0000404207 scopus 로고    scopus 로고
    • 4a Fukuzawa, S.-i.; Fujimoto, K.; Komuro, Y.; Matsuzawa, H. Org. Lett. 2002, 4, 707-709.
    • 4a Fukuzawa, S.-i.; Fujimoto, K.; Komuro, Y.; Matsuzawa, H. Org. Lett. 2002, 4, 707-709.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.