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Volumn 48, Issue 7, 2007, Pages 1105-1108

Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of a d-ribo-phytosphingosine derivative

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; ALKYL GROUP; ALLYLAMINE DERIVATIVE; METHYL CHLORIDE; OSMIUM TETRAOXIDE; PHYTOSPHINGOSINE;

EID: 33846213597     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.084     Document Type: Article
Times cited : (26)

References (45)
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    • 2042464342 scopus 로고    scopus 로고
    • For the stereo-controlled osmylations of cyclic allylic amino derivatives, see: Chem. Abstr., 1998, 129, 202696z
    • For the stereo-controlled osmylations of cyclic allylic amino derivatives, see:. Oh J.S., Hong Y.S., and Kim Y.G. J. Ind. Eng. Chem. 3 (1997) 326 Chem. Abstr., 1998, 129, 202696z
    • (1997) J. Ind. Eng. Chem. , vol.3 , pp. 326
    • Oh, J.S.1    Hong, Y.S.2    Kim, Y.G.3
  • 18
    • 0024802464 scopus 로고
    • For the solvent effect on the facial stereoselectivity of osmylations, see:
    • For the solvent effect on the facial stereoselectivity of osmylations, see:. Poli G. Tetrahedron Lett. 30 (1989) 7385
    • (1989) Tetrahedron Lett. , vol.30 , pp. 7385
    • Poli, G.1
  • 21
    • 33846234618 scopus 로고    scopus 로고
    • 3a and 5.
  • 22
    • 33846215038 scopus 로고    scopus 로고
    • note
    • 2 column separation was determined by converting separately into the following cyclic compounds and comparing their coupling constants. The small coupling constants of 4-5 Hz as in 8syn are generally assigned to the trans oxazolidinones [(a) Ref. 1a and references cited therein. (b) Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles, 1992, 33, 1051 and references cited therein. (c) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439]. The large coupling constants of 8-10 Hz as in 8anti are typically due to the diaxial relationship between the two adjacent protons in six-membered rings [Pretsch, E.; Bühlmann, P.; Affolter, C.; Structure Determination of Organic Compounds, 3rd ed.; Springer: Berlin, 2000; pp 161-198]. The sense of asymmetric induction caused by the N,N-diBoc group was confirmed further by stereoselective syntheses of the known derivatives of both diastereomers, d-ribo- and l-arabino-phytosphingosine, from each dihydroxylation product as described in the text.{A figure is presented}.
  • 23
    • 0030599656 scopus 로고    scopus 로고
    • The slow reaction rates of the osmylations of the conjugated N,N-dibenzyl-(E)-allylic amines were also reported:
    • The slow reaction rates of the osmylations of the conjugated N,N-dibenzyl-(E)-allylic amines were also reported:. Reetz M.T., Strack T.J., Mutulis F., and Goddard R. Tetrahedron Lett. 37 (1996) 9293
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9293
    • Reetz, M.T.1    Strack, T.J.2    Mutulis, F.3    Goddard, R.4
  • 25
    • 33748542524 scopus 로고
    • For reviews of allylic strains, see:
    • For reviews of allylic strains, see:. Johnson R. Chem. Rev. 68 (1968) 375
    • (1968) Chem. Rev. , vol.68 , pp. 375
    • Johnson, R.1
  • 30
    • 0036231270 scopus 로고    scopus 로고
    • For a review of previous synthetic efforts, see:
    • For a review of previous synthetic efforts, see:. Howell A.R., and Ndakala A.J. Curr. Org. Chem. 6 (2002) 365
    • (2002) Curr. Org. Chem. , vol.6 , pp. 365
    • Howell, A.R.1    Ndakala, A.J.2
  • 45
    • 33846261902 scopus 로고    scopus 로고
    • note
    • 3)].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.