Isopinoeampheylchloroborane: A promising new reagent for asymmetric cyclic hydroboration. A simple procedure to convert 1-allyl-1-cyclohexene into trans-1-decalone of ≥99% optical purity

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 1906-1907

  Brown, Herbert C ^a   Mahindroo, Verinder K ^a,b   Dhokte, Ulhas P ^a  

^a PURDUE UNIVERSITY   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001146551     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952143n     Document Type: Article

References (26)

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8. This molecule actually exists in solution as a dimer. However, it is convenient to represent in the monomeric form.
9. Brown, H. C.; Jadhav, P. K.; Mandal, A. K. J. Org. Chem. 1982, 47, 5074.
10. Djerassi, C.; Staunton, J. J. Am. Chem. Soc. 1961, 83, 736.
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15. (b) Brown, H. C.; Carlson, B. A. J. Org. Chem. 1973, 38, 2422.
16. 8 have established the absolute configuration of trans-1-decalone (5). Thus, in accord with the sign of the rotation of the this ketone 5, obtained by the asymmetric cyclic hydroboration, its absolute configuration should be (9R,10S).
17. Houk, K. N.; Rondan, N. G.; Wu, Y.-D.; Metz, J. T.; Paddon-Row, M. N. Tetrahedron 1984, 40, 2257.
18. Egger, M.; Keese, R. Helv. Chim. Acta 1987, 70, 1843.
19. 2. Dhokte, U. P.; Kulkarni, S. V.; Brown, H. C. Research in progress.
20. (a) Kulkarni, S. U.; Lee, H. D.; Brown, H. C. J. Org. Chem. 1980, 45, 4542.
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23. The DCME reaction-oxidation process transforms borinate esters 10 into ketones and trialkylboranes into a tertiary alcohols.
24. Brown, H. C.; Ramachandran, P. V.; Chandrasekharan, J. Heteroatom. Chem. 1995, 6, 117.
25. Soundararajan, R.; Matteson, D. S. Organometallics 1995, 14, 4157.
26. D -10 ±1 (c 0.55, EtOH)).