Palladium complex catalyzed asymmetric allylic substitutions with nitromethane: Enantioselectivities exceeding 99.9% ee

Angewandte Chemie (International Edition in English)

Volumn 34, Issue 23, 1996, Pages 2687-2689

  Rieck, Heiko ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Asymmetric syntheses; Catalysis; Nitro compounds; Palladium compounds; Substitutions

Indexed keywords

EID: 33751133409     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199526871     Document Type: Article

References (19)

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3. J. Sprinz, C. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; G. J. Dawson, C. G. Frost, J. M. J. Williams, S. J. Coote, Tetrahedron Lett. 1993, 34, 3149-3150.
4. J. Sprinz, C. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; G. J. Dawson, C. G. Frost, J. M. J. Williams, S. J. Coote, Tetrahedron Lett. 1993, 34, 3149-3150.
5. J. Sprinz, C. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; G. J. Dawson, C. G. Frost, J. M. J. Williams, S. J. Coote, Tetrahedron Lett. 1993, 34, 3149-3150.
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8. P. Aleksandrowicz, H. Piotrowska, W. Sas, Tetrahedron 1982, 38, 1321-1327; P. A. Wade, S. D. Morrow, S. A. Hardinger, J. Org. Chem. 1982, 47, 365-367; J. E. Bäckvall, S. E. Byström, J. E. Nyström, ibid. 1992, 57, 1588-1591; D. R. Deardorff, M. J. Shulman, J. E. Sheppeck, Tetrahedron Lett. 1989, 30, 6625-6628; M. R. Peel, D. D. Sternbach, M. R. Johnson, J. Org. Chem. 1991, 56, 4990-4993; B. M. Trost, L. Li, S. D. Guile, J. Am. Chem. Soc. 1992, 114, 8745-8747.
9. P. Aleksandrowicz, H. Piotrowska, W. Sas, Tetrahedron 1982, 38, 1321-1327; P. A. Wade, S. D. Morrow, S. A. Hardinger, J. Org. Chem. 1982, 47, 365-367; J. E. Bäckvall, S. E. Byström, J. E. Nyström, ibid. 1992, 57, 1588-1591; D. R. Deardorff, M. J. Shulman, J. E. Sheppeck, Tetrahedron Lett. 1989, 30, 6625-6628; M. R. Peel, D. D. Sternbach, M. R. Johnson, J. Org. Chem. 1991, 56, 4990-4993; B. M. Trost, L. Li, S. D. Guile, J. Am. Chem. Soc. 1992, 114, 8745-8747.
10. P. Aleksandrowicz, H. Piotrowska, W. Sas, Tetrahedron 1982, 38, 1321-1327; P. A. Wade, S. D. Morrow, S. A. Hardinger, J. Org. Chem. 1982, 47, 365-367; J. E. Bäckvall, S. E. Byström, J. E. Nyström, ibid. 1992, 57, 1588-1591; D. R. Deardorff, M. J. Shulman, J. E. Sheppeck, Tetrahedron Lett. 1989, 30, 6625-6628; M. R. Peel, D. D. Sternbach, M. R. Johnson, J. Org. Chem. 1991, 56, 4990-4993; B. M. Trost, L. Li, S. D. Guile, J. Am. Chem. Soc. 1992, 114, 8745-8747.
11. P. Aleksandrowicz, H. Piotrowska, W. Sas, Tetrahedron 1982, 38, 1321-1327; P. A. Wade, S. D. Morrow, S. A. Hardinger, J. Org. Chem. 1982, 47, 365-367; J. E. Bäckvall, S. E. Byström, J. E. Nyström, ibid. 1992, 57, 1588-1591; D. R. Deardorff, M. J. Shulman, J. E. Sheppeck, Tetrahedron Lett. 1989, 30, 6625-6628; M. R. Peel, D. D. Sternbach, M. R. Johnson, J. Org. Chem. 1991, 56, 4990-4993; B. M. Trost, L. Li, S. D. Guile, J. Am. Chem. Soc. 1992, 114, 8745-8747.
12. P. Aleksandrowicz, H. Piotrowska, W. Sas, Tetrahedron 1982, 38, 1321-1327; P. A. Wade, S. D. Morrow, S. A. Hardinger, J. Org. Chem. 1982, 47, 365-367; J. E. Bäckvall, S. E. Byström, J. E. Nyström, ibid. 1992, 57, 1588-1591; D. R. Deardorff, M. J. Shulman, J. E. Sheppeck, Tetrahedron Lett. 1989, 30, 6625-6628; M. R. Peel, D. D. Sternbach, M. R. Johnson, J. Org. Chem. 1991, 56, 4990-4993; B. M. Trost, L. Li, S. D. Guile, J. Am. Chem. Soc. 1992, 114, 8745-8747.
13. J. P. Genet, S. Grisoni, Tetrahedron Lett. 1988, 36, 4543-4546.
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15. 2S/λ > 300 nm, benzene).
16. For other examples of double asymmetric induction, see; S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Im. Ed. Engl. 1985, 24, 1-30.
17. For other examples of double asymmetric induction, see; S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Im. Ed. Engl. 1985, 24, 1-30.
18. 2 is probably small.
19. dba = 1,5-Diphenyl-1,4-pentadien-3-one.