Asymmetric Carbon-Carbon Bond Formation via B-Allyldiisopinocampheylborane. Simple Synthesis of Secondary Homoallylic Alcohols with Excellent Enantiomeric Purities

Journal of the American Chemical Society

Volumn 105, Issue 7, 1983, Pages 2092-2093

  Brown, Herbert C ^a   Jadhav, Prabhakar K ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845550192     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00345a085     Document Type: Article

References (10)

1. Research associate on Grant 2R01 GM 10937-20 from the National Institutes of Health.
2. (a) Mikhailov, B.M. Organomet. Chem. Rev. Sect. A 1972, 8, 1. (b) Kramer, G.W.; Brown, H.C.J. Organomet. Chem. 1977, 132, 9. (c) Kramer, G.W.; Brown, H.C.J. Org. Chem. 1977, 42, 2292.
3. (a) Herold, T.; Hoffmann, R.W. Angew. Chem. Int. Ed. Engl. 1978, 17, 768. (b) Herold, T.; Schrott, U.; Hoffmann, R.W. Chem. Ber. 1981, 114, 359. (c) Hoffmann, R.W.; Herold, T. Chem. Ber. 1981, 114, 375.
4. Midland, M.M.; Preston, S.B. J. Am. Chem. Soc. 1982, 104, 2330.
5. Brown, H.C.; Ravindran, N. J. Am. Chem. Soc. 1972, 94, 2112.
6. Brown, H.C.; Desai, M.C.; Jadhav, P.K. J. Org. Chem. 1982, 47, 5065.
7. Brown, H.C.; Yoon, N.M. Isr. J. Chem. 1977, 15, 12.
8. For handling air- and moisture-sensitive compounds, See: Brown, H.C.; Kramer, G.W.; Levy, A.B.; Midland, M.M. Organic Syntheses via Boranes”; Wiley-Interscience: New York, 1975; p. 191.
9. Brown, H.C.; Jadhav, P.K.; Mandal, A.K. Tetrahedron 1981, 37, 3547.
10. Dale, J.A.; Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512.