Hydroboration of mono-substituted allenes: A general synthetic route to the higher crotylboranes and anti-3-alkyl/aryl-4-hydroxy-1-alkenes

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 219-222

  Narla, Gowriswari ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031030668     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02255-1     Document Type: Article

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13. (b) Martin, S. F; Guinn, D. E. Synthesis 1991, 245.
14. (c) Hoffmann, R. W. Synthesis 1987, 489.
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20. (c) The chemical shift of the olefinic protons defer for the two diastereomers. In the case of entries 5 and 6, δ 4.97 (dd, 1H) and 5.34-5.44 (m, 1H) for syn isomer and δ 5.24 (dd, 1H) and 5.81 (dd, 1H) for anti isomer. For entries 7 and 8, δ 5.82 (ddd, 1H) for syn isomer and δ 6.15 (ddd, 1H) for anti isomer.
21. Brown, H. C.; Liotta, R.; Kramer, G. W. J. Am. Chem. Soc. 1979, 101, 2966.
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23. 3. The coupling constant of the olefinic proton, on decoupling with the adjacent methynyl proton of the cyclohexyl ring, is 14.8 Hz. This indicates that the geometry of the double bond is trans.
24. Brown, H. C; Dhar, R. K; Ganesan, K; Singaram, B. J. Org. Chem. 1992, 57, 499.
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26. 1H NMR analysis and capillary GC analysis.
27. Skattebol, L. Acta Chem. Scand. 1963, 17, 1683.