Cyanoborohydride supported on an anion exchange resin as a selective reducing agent

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 24, 1978, Pages 1088-1089

  Hutchins, Robert O ^a   Natale, Nicholas R ^a   Taffer, Ira M ^a  

^a DREXEL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049095176     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39780001088     Document Type: Article

References (16)

1. E. C. Blossey and D. C. Neckers, eds., ‘Solid Phase Synthesis,’ Dowden, Hutchinson, and Ross, Stroudsburg, PA, 1975
2. E. G. Overberger and K. N. Sannes, Angew. Chem. Internat. Edn., 1974, 13, 99
3. borohydride anion exchange resins have been described, D. M. Perrier, R. R. Benerito, and R. H. Steele, U. S. P. 4,032,293 (1977)
4. H. W. Gibson and F. Courtney, J.C.S. Chem. Comm., 1977, 815.
5. For a review of cyanoborohydride chemistry see, C. F. Lane, Synthesis, 1975, 135
6. recent applications include: (b) dehaloge-nations, R. O. Hutchins, D. Kandasamy, C. Maryanoff, D. Masilamani, and B. Maryanoff, J. Org. Chem., 1977, 42, 82
7. conversion of unsaturated carbonyls into: (c) allylic alcohols, R. O. Hutchins and D. Kandasamy, J. Org. Chem., 1975, 40, 2530
8. rearranged alkenes, R. O. Hutchins, M. Kacher, and L. Rua, J. Org. Chem., p. 923
9. reduction of heterocycles, G. W. Gribble and P. W. Heald, Synthesis, 1975, 650
10. E. Booker and U. Eisner, J.C.S. Perkin I, 1975, 929
11. J. Berger, F. Davidson, and G. Langford, J. Medicin. Chem., 1977, 20, 600
12. reduction of polar alkenes to hydrocarbons, R. O. Hutchins, D. Rotstein, N. Natale, J. Fanelli, and D. Dimmel, J. Org. Chem., 1976, 41, 3328
13. reduction of acetals to ethers, D. A. Home and A. Jordan, Tetrahedron Letters, 1978, 1357.
14. For a review of selective reductions with hydride transfer reagents see, E. R. H. Walker, Chem. Soc. Rev., 1976, 5, 23.
15. M. M. Kreevoy, R. F. Borch, and J. E. C. Hutchins, U.S.P. 3,873,621 (1975).
16. R. F. Borch and A. I. Hassid, J. Org. Chem., 1972, 37, 1673.