Hydroboration, followed by water addition of benchrotrenic alkenes. Formal dihydrogen addition

Journal of Organometallic Chemistry

Volumn 525, Issue 1-2, 1996, Pages 283-286

  Caro, Bertrand ^a   Sénéchal Tocquer, Marie Claude ^a   Sénéchal, Denis ^a   Guen, Françoise Robin Le ^a  

^a CNRS   (France)

Author keywords

Benchrotrenic alkenes; Boron; Carbonyl; Chromium; Dihydrogen; Hydroboration

Indexed keywords

EID: 0030588838     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(96)06329-2     Document Type: Article

References (21)

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3. [2] (a) K.M. Nicholas and R. Pettit, Tetrahedron Lett., (1971) 3475-3478;
4. (b) C.H. Mauldin, E.R. Biehl and P.C. Reeves, Tetrahedron Lett., (1972) 2955-2958.
5. (c) R. Gree, Synthesis, (1989) 341-355.
6. (d) C. Lo Sterzo and G. Ortaggi, J. Chem. Soc. Perkin Trans. II, (1984) 345-348.
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9. [5] Mixture of diastereoisomeres.
10. [6] In this case, an hydrolysis performed on ice allowed the formation of the 2-endo-methyl, 1-exo-tetralol complex (20% yield) together with 7c (55% yield) as in (Scheme 2).
11. [7] H.C. Brown and R.L. Sharp, J. Amer. Chem. Soc., 88 (1966) 5851-5854.
12. [8] A.J. Weinheimer and W.E. Marsico, J. Org. Chem., 27 (1962) 1926.
13. 2, NaOH addition is performed at -78°C, the formation of the hydrogenated products decreases: M. Franck-Neumann, D. Martina and M.P. Heitz, J. Organomet. Chem., 301 (1986) 61-77.
14. [10] See for example: M.C. Senechal-Tocquer, D. Senechal, J.Y. Le Bihan, D. Gentric and B. Caro, Bull. Soc. Chim. Fr., 129 (1992) 121-136.
15. [11] Percentages refer to the Cα and Cβ boron bond formation.
16. [12] Values refer to the α and β alcools obtained by alkaline hydroperoxide oxidation of the α and β alkylboranes.
17. [13] H.C. Brown, Hydroboration, Benjamin, New York, 1962.
18. [14] H.C. Brown and R.L. Sharp, J, Amer. Chem. Soc., 90 (1968) 2915-2927.
19. [15] G.L. Larson, D. Hernandez and A. Hernandez, J. Organomet. Chem., 76 (1974) 9-16.
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21. [17] For a comparison note that the 1-methylcyclohexene and the 1-methylcyclopentene gave, like 6d, a unique Cβ-B bond formation [13].