A Highly Diastereoselective Addition of (E)- and (Z)-Crotyldiisopinocampheylboranes to α-Substituted Aldehydes

Journal of Organic Chemistry

Volumn 52, Issue 16, 1987, Pages 3701-3702

  Brown, Herbert C ^a   Bhat, Krishna S ^a   Randad, Ramnarayan S ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001383044     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00392a043     Document Type: Article

References (10)

1. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed; Academic: New York, 1984; Vol. 3, p 111. Mukaiyama, T. Org. React. (N. Y.) 1982, 28, 203. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
2. Hoffmann, R. W.; Weidmann, U. Chem. Ber. 1985,118, 3966 and references cited therein. Hoffmann, R. W.; Ditrich, K.; Froech, S. Tetrahedron 1985,41, 5517; Tetrahedron Lett. 1984, 25, 1781. Hoffmann, R. W.; Endesfelder, A.; Zeiss, H. J. Carbohydr. Res. 1983,123, 320. Hoffmann, R. W.; Zeiss, H. J. ; Ladner, W.; Tabche, S. Chem. Ber. 1982, 115, 2357. Hoffmann, R. W.; Ladner, W. Tetrahedron Lett. 1979, 4653.
3. Roush, W. R.; Adam, M. A.; Walts, A. E.; Harris, D. J. J. Am. Chem. Soc. 1986,108, 3422 and references cited therein. Roush, W. R.; Halterman, R. L. Chem. Ber. 294. Roush, W. R.; Adam, M. A.; Harris, D. J. J. Org. Chem. 1985,50, 2000. Roush, W. R.; Walts, A. E.; Hoong, L. K. J. Am. Chem. Soc. 1985, 107. 8186.
4. Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985,24,1. McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3,125. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556. Yamamoto, Y.; Maruyama, K. Heterocycles 1982, 18, 357. Masamune, S.; Hirama, M.; Mori, S. J. Am. Chem. Soc. 1981,103, 1568. Bartlett, P. A. Tetrahedron 1980, 36, 2.
5. Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986,108, 5919. Yamamoto, Y.; Yatagai, H.; Maruyama, K. Angew. Chem., Int. Ed. Engl. 1981,103, 3229. Yatagai, H.; Yamamoto, Y.; Maruyama, K. Angew. Chem., Int. Ed. Engl. 1980, 102, 4548. Hoffman, R. W.; Zeiss, H. J. Angew. Chem., Int. Ed. Engl. 1979,18,306.
6. Masamune, S.; Choy, W. Aldrichimica Acta 1982,15, 47. Brooks, D. W.; Kellogg, R. P. Tetrahedron Lett. 1982,23,4991. Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre, D. J.; Bartroli, J. Pure Appl. Chem. 1981, 53, 110.
7. Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1987, 52, 319.
8. tation with enthanolamine. Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1985. 107, 2564.
9. For techniques, see: Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis via Boranes; Wiley-Interscience: New York, 1975; p 191.
10. Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. Org. Chem. 1987, 52, 316.