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Volumn 69, Issue 16, 2004, Pages 5307-5313

Highly Stereoselective approach to Alk-2-yne-1,4-diols by oxazaborolidine-mediated reduction of Alk-2-yne-1,4-diones

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; COBALT COMPOUNDS; DERIVATIVES; ISOMERS; REDUCTION; STEREOCHEMISTRY;

EID: 3542997455     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0495687     Document Type: Article
Times cited : (12)

References (63)
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    • 4 reduction and partial hydrogenation, respectively (see ref 1).
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    • For a review on substrate-directable chemical reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
    • (1993) Chem. Rev. , vol.93 , pp. 1307-1370
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 9
    • 0027245910 scopus 로고
    • Current preparations of enantiopure saturated 1,4-diols include: Enzymatic resolutions of mixtures of meso and racemic isomers: (a) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry 1993, 4, 925-930.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 925-930
    • Mattson, A.1    Öhrner, N.2    Hult, K.3    Norin, T.4
  • 14
  • 16
    • 0000956274 scopus 로고
    • Microbial reduction of diketones using baker's yeast: (h) Lieser, J. K. Synth. Commun. 1983, 13, 765-767.
    • (1983) Synth. Commun. , vol.13 , pp. 765-767
    • Lieser, J.K.1
  • 19
  • 29
    • 3543040999 scopus 로고    scopus 로고
    • note
    • In many cases, the aldehyde is partially consumed in the formation of self-condensation aldol products.
  • 33
    • 0032480917 scopus 로고    scopus 로고
    • In this connection, it should be noted that the oxazaborolidine-mediated reduction of the related (E)-alk-2-ene-1,4-diones affords 1,4-diols 2 in good yields and enantioselectivities but, in general, suffers from low diastereoselectivities (dl/meso ratio from 5.6:1 to ∼1:1). In contrast, (Z)-alk-2-ene-1,4-diones give low yields of the desired (Z)-1,4-diol 3 under the same conditions. See: Bach, J.; Berenguer, R.; Garcia, J.; López, M.; Manzanal, J.; Vilarrasa, J. Tetrahedron 1998, 54, 14947-14962.
    • (1998) Tetrahedron , vol.54 , pp. 14947-14962
    • Bach, J.1    Berenguer, R.2    Garcia, J.3    López, M.4    Manzanal, J.5    Vilarrasa, J.6
  • 34
    • 0002736658 scopus 로고
    • For a discussion of this statistical effect applied to two-directional chain syntheses, see: Poss C. S.; Schreiber S. L. Acc. Chem. Res. 1994, 27, 9-17.
    • (1994) Acc. Chem. Res. , vol.27 , pp. 9-17
    • Poss, C.S.1    Schreiber, S.L.2
  • 38
    • 33646850080 scopus 로고
    • Sudweeks, W. B.; Broadbent, H. S. J. Org. Chem. 1975, 40, 1131-1136. These authors described the preparation of 1d and 1e in 32% and 31% using the magnesium acetylide. We obtained better results (76% and 98% yield, respectively) by using the dilithium acetylide. However, when α-unbranched aldehydes as propanal were used, much lower yields were recorded.
    • (1975) J. Org. Chem. , vol.40 , pp. 1131-1136
    • Sudweeks, W.B.1    Broadbent, H.S.2
  • 39
    • 3543034374 scopus 로고    scopus 로고
    • note
    • Reduction of diketone 5f using 0.2 mmol of catalyst led to a complex mixture from which diol (R,R)-1f was isolated in low yield. This disappointing result was not completely unexpected in the light of our previous experience in the reduction of the related 1,4-diphenylbut-2-ene-1,4-dione (see ref 12).
  • 40
    • 3543031960 scopus 로고    scopus 로고
    • note
    • 2, Pt/C) of 1 with that given in the literature (see refs 12 and 14 and references therein).
  • 45
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    • Transformation of 1a into 9a by treatment with bromine in chloroform was described almost a century ago: (a) Dupont, M. G. C. R. Acad. Sci. 1909, 149, 1381-1383.
    • (1909) C. R. Acad. Sci. , vol.149 , pp. 1381-1383
    • Dupont, M.G.1
  • 48
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    • The use of bromine in the presence of Hünig's base has been also reported: (d) Adjé, N.; Breuilles, P.; Uguen, D. Tetrahedron Lett. 1993, 34, 4631-4634.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4631-4634
    • Adjé, N.1    Breuilles, P.2    Uguen, D.3
  • 49
    • 3543014134 scopus 로고    scopus 로고
    • note
    • i symmetry). In contrast, the dipole moment for the minimum energy conformations of dl-2a and dl-9a are 0.01 and 2.46 D, respectively.
  • 58
    • 3542996613 scopus 로고    scopus 로고
    • note
    • 4 reduction of diketone 5g gave a ∼1:1 mixture of dl-1g and meso-1g.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.