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Volumn 73, Issue 16, 2008, Pages 6292-6298

Diastereoselective synthesis of useful building blocks by crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKS; CHEMICAL EQUATIONS; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; DIASTEREOSELECTIVE SYNTHESIS; GOOD YIELDS; METHYL SUBSTITUENTS; PROPANAL;

EID: 50149093469     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801106b     Document Type: Article
Times cited : (13)

References (52)
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    • For recent reviews on organotrifluoroborates, see: a
    • For recent reviews on organotrifluoroborates, see: (a) Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313-4327.
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    • and references cited therein
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    • Molander, G.A.1    Biolatto, B.2
  • 20
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    • Synthesis of a stereotriad having the identical vinyl ends, using the coupling of vinyloxiranes and potassium crotyltrifluoroborates, has been reported. See
    • Synthesis of a stereotriad having the identical vinyl ends, using the coupling of vinyloxiranes and potassium crotyltrifluoroborates, has been reported. See: Lautens, M., Ouellet, S. G., Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079-4082.
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    • Aldehydes 1 were prepared from 2-methyl-1,3-propanediol in two steps. For 1b see: (a) Kiyooka, S.; Shahid, K. A.; Goto, F.; Okazaki, M.; Shuto, Y. J. Org. Chem. 2003, 68, 7967-7978.
    • Aldehydes 1 were prepared from 2-methyl-1,3-propanediol in two steps. For 1b see: (a) Kiyooka, S.; Shahid, K. A.; Goto, F.; Okazaki, M.; Shuto, Y. J. Org. Chem. 2003, 68, 7967-7978.
  • 22
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    • For 1d see: (b) Kiyooka, S. Tetrahedron: Asymmetry 2003, 14, 2897-2910. 1a and 1c were similarly prepared.
    • For 1d see: (b) Kiyooka, S. Tetrahedron: Asymmetry 2003, 14, 2897-2910. 1a and 1c were similarly prepared.
  • 23
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    • 1H NMR comparisons with the reported data. For 3b-6b and 3d-6d see: (a) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348-6359.
    • 1H NMR comparisons with the reported data. For 3b-6b and 3d-6d see: (a) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348-6359.
  • 24
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    • 1H NMR spectra with 3d-6d and mechanistic considerations.
  • 25
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    • 7a was prepared from methacrolein and 2,2-dimethyl-1,3-propanediol according to the reported procedure. See: (a) Kelly, T. R.; Fu, Y.; Xie, R. L. Tetrahedron Lett. 1999, 40, 1857-1860.
    • 7a was prepared from methacrolein and 2,2-dimethyl-1,3-propanediol according to the reported procedure. See: (a) Kelly, T. R.; Fu, Y.; Xie, R. L. Tetrahedron Lett. 1999, 40, 1857-1860.
  • 26
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    • For (-)-7b see: (b) Smith, A. B., III; Adams, C. M.; Barbosa, S. A. L.; Degnan, A. P. Proc. Nat. Acc. Sci. 2004, 101, 12042-12047.
    • For (-)-7b see: (b) Smith, A. B., III; Adams, C. M.; Barbosa, S. A. L.; Degnan, A. P. Proc. Nat. Acc. Sci. 2004, 101, 12042-12047.
  • 27
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    • Racemate 7b was prepared from 1d according to the same procedure, (c) For preparation of 7c and 7c′, see the Supporting Information.
    • Racemate 7b was prepared from 1d according to the same procedure, (c) For preparation of 7c and 7c′, see the Supporting Information.
  • 28
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    • Structure determination of the adducts, see the Supporting Information
    • Structure determination of the adducts, see the Supporting Information.
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    • The β-substituent effects on the aldehyde π-facial selectivity are suggested in the previous reports, see: (a) Hoffmann, R. W, Weidmann, U. Chem. Ber. 1985, 118, 3966-3979
    • The β-substituent effects on the aldehyde π-facial selectivity are suggested in the previous reports, see: (a) Hoffmann, R. W.; Weidmann, U. Chem. Ber. 1985, 118, 3966-3979.
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    • 4, MeOH) and the resulting alcohol was identified on the basis of the spectral data reported in the same paper. See the Supporting Information.
    • 4, MeOH) and the resulting alcohol was identified on the basis of the spectral data reported in the same paper. See the Supporting Information.
  • 48
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.