메뉴 건너뛰기




Volumn , Issue 13, 2004, Pages 2863-2867

Reduction of carbonyl compounds by lanthanide metal/2-propanol: In-situ generation of samarium isopropyloxide for stereoselective Meerwein-Ponndorf- Verley reduction

Author keywords

Lanthanides; Meerwein Ponndorf Verley reduction; Reductions; Samarium; Samarium alkoxide

Indexed keywords

1 PHENYLETHANOL; 2 PROPANOL; ACETOPHENONE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; CESIUM; CYCLOHEXANONE DERIVATIVE; IODINE; KETONE DERIVATIVE; LANTHANIDE; LANTHANUM; METAL; SAMARIUM; YTTERBIUM;

EID: 4544384173     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400030     Document Type: Article
Times cited : (39)

References (43)
  • 2
    • 37049118036 scopus 로고
    • [1a] D. F. Evans, G. V. Fazakerley, R. F. Phillips, J. Chem. Soc., Chem. Commun. 1970, 244; J. Chem. Soc., A 1971, 1931.
    • (1971) J. Chem. Soc., A , pp. 1931
  • 26
    • 0010077452 scopus 로고
    • For reviews: [8a] G. A. Molander, Chem. Rev. 1992, 92, 29; G. A. Molander, Org. React. 1994, 46, 211.
    • (1992) Chem. Rev. , vol.92 , pp. 29
    • Molander, G.A.1
  • 27
    • 0010077452 scopus 로고
    • For reviews: [8a] G. A. Molander, Chem. Rev. 1992, 92, 29; G. A. Molander, Org. React. 1994, 46, 211.
    • (1994) Org. React. , vol.46 , pp. 211
    • Molander, G.A.1
  • 28
    • 2142715741 scopus 로고    scopus 로고
    • [8b] G. A. Molander, C. H. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. H. Harris, Tetrahedron 1998, 54, 3321.
    • (1996) Chem. Rev. , vol.96 , pp. 307
    • Molander, G.A.1    Harris, C.H.2
  • 29
    • 0032473838 scopus 로고    scopus 로고
    • [8b] G. A. Molander, C. H. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. H. Harris, Tetrahedron 1998, 54, 3321.
    • (1998) Tetrahedron , vol.54 , pp. 3321
    • Molander, G.A.1    Harris, C.H.2
  • 30
    • 0002468910 scopus 로고    scopus 로고
    • Influence of solvents or additives on the organic chemistry mediated by diiodosamarium
    • (Ed.: S. Kobayashi), Springer: Berlin, Heidelberg
    • [8c] H. B. Kagan. J.-L. Namy, in: "Influence of Solvents or Additives on the Organic Chemistry mediated by Diiodosamarium", Lanthanides: Chemistry and Use in Organic Synthesis (Ed.: S. Kobayashi), Springer: Berlin, Heidelberg, 1999; pp. 155-198.
    • (1999) Lanthanides: Chemistry and Use in Organic Synthesis , pp. 155-198
    • Kagan, H.B.1    Namy, J.-L.2
  • 33
    • 0000139706 scopus 로고
    • The darkened solution may show the formation of a lanthanide isopropyloxide. Lanthanide isopropyloxides have been prepared by the direct reaction of a lanthanide amalgam with 2-propanol: K. S. Mazdiyasni, C. T. Lynch, J. S. Smith, Inorg. Chem. 1966, 5, 342; [8b] G. A. Molander, C. H. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. H. Harris, Tetrahedron 1998, 54, 3321.
    • (1966) Inorg. Chem. , vol.5 , pp. 342
    • Mazdiyasni, K.S.1    Lynch, C.T.2    Smith, J.S.3
  • 34
    • 33947297511 scopus 로고
    • The darkened solution may show the formation of a lanthanide isopropyloxide. Lanthanide isopropyloxides have been prepared by the direct reaction of a lanthanide amalgam with 2-propanol: K. S. Mazdiyasni, C. T. Lynch, J. S. Smith, Inorg. Chem. 1966, 5, 342; [8b] G. A. Molander, C. H. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. H. Harris, Tetrahedron 1998, 54, 3321.
    • (1970) Inorg. Chem. , vol.9 , pp. 2783
    • Brown, L.M.1    Mazdiyasni, K.S.2
  • 36
    • 4544274561 scopus 로고
    • Deoxygenation of α-methoxy ketones and esters has been reported: G. A. Molander, G. Hahn, J. Org. Chem. 1986, 51, 1136; K. Kusuda, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1989, 30, 2945.
    • (1986) J. Org. Chem. , vol.51 , pp. 1136
    • Molander, G.A.1    Hahn, G.2
  • 37
    • 0000856232 scopus 로고
    • Deoxygenation of α-methoxy ketones and esters has been reported: G. A. Molander, G. Hahn, J. Org. Chem. 1986, 51, 1136; K. Kusuda, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1989, 30, 2945.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2945
    • Kusuda, K.1    Inanaga, J.2    Yamaguchi, M.3
  • 38
    • 4544268131 scopus 로고    scopus 로고
    • note
    • Our result differed from Kagan's report, in which the cis alcohol was the major product (cis/trans = 72:28) after repetition of several experiments. See ref.[11]
  • 39
    • 0001143623 scopus 로고
    • Lanthanide isopropyloxide-mediated MPV reductions have been reported: J.-L. Namy, J. Souppe, J. Collin, H. B. Kagan, J. Org. Chem. 1984, 49, 2045; A. Lebrun, J.-L. Namy, H. B. Kagan, Tetrahedron Lett. 1991, 32, 2355; T. Okano, M. Matsuoka, S. Kinoshita, M. Kiji, Nippon Kagaku Kaishi, 1993, 487.
    • (1984) J. Org. Chem. , vol.49 , pp. 2045
    • Namy, J.-L.1    Souppe, J.2    Collin, J.3    Kagan, H.B.4
  • 40
    • 0025864813 scopus 로고
    • Lanthanide isopropyloxide-mediated MPV reductions have been reported: J.-L. Namy, J. Souppe, J. Collin, H. B. Kagan, J. Org. Chem. 1984, 49, 2045; A. Lebrun, J.-L. Namy, H. B. Kagan, Tetrahedron Lett. 1991, 32, 2355; T. Okano, M. Matsuoka, S. Kinoshita, M. Kiji, Nippon Kagaku Kaishi, 1993, 487.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2355
    • Lebrun, A.1    Namy, J.-L.2    Kagan, H.B.3
  • 41
    • 85016542021 scopus 로고
    • Lanthanide isopropyloxide-mediated MPV reductions have been reported: J.-L. Namy, J. Souppe, J. Collin, H. B. Kagan, J. Org. Chem. 1984, 49, 2045; A. Lebrun, J.-L. Namy, H. B. Kagan, Tetrahedron Lett. 1991, 32, 2355; T. Okano, M. Matsuoka, S. Kinoshita, M. Kiji, Nippon Kagaku Kaishi, 1993, 487.
    • (1993) Nippon Kagaku Kaishi , pp. 487
    • Okano, T.1    Matsuoka, M.2    Kinoshita, S.3    Kiji, M.4
  • 42
    • 4544311309 scopus 로고    scopus 로고
    • note
    • 2CDOH (99.8%), and obtained a > 98% deuterated 1-phenylethanol, PhCD(OH)Me. This result suggests that hydride transfer occurs from the samarium isopropyloxide.
  • 43
    • 0001767033 scopus 로고
    • It has been reported that the samarium alkoxide of the amino alcohol 7 is an efficient catalyst for asymmetric MPV reduction: D. A. Evans, S. G. Nelson, M. R. Gand, A. R. Muci, J Am. Chem. Soc. 1993, 115, 9800.
    • (1993) J Am. Chem. Soc. , vol.115 , pp. 9800
    • Evans, D.A.1    Nelson, S.G.2    Gand, M.R.3    Muci, A.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.