Cu-catalyzed enantioselective conjugate additions of alkyl zinc reagents to unsaturated N-acyloxazolidinones promoted by a chiral triamide phosphane

Angewandte Chemie - International Edition

Volumn 42, Issue 11, 2003, Pages 1276-1279

  Hird, Alexander W ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

Alkyl metal compounds; Asymmetric catalysis; Conjugate addition; Copper; Enantioselectivity

Indexed keywords

CARBONYLATION; CATALYSIS; ZINC;

CARBONYL COMPOUNDS;

COPPER;

ALKYL GROUP; COPPER; LIGAND; N ACYLOXAZOLIDINONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PHOSPHATE; TRIAMIDE PHOSPHANE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; LIGAND BINDING; METAL BINDING; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ALKYLATION; AMINO ACIDS; CATALYSIS; COPPER; MOLECULAR STRUCTURE; OXAZOLIDINONES; PHOSPHINES; STEREOISOMERISM; ZINC COMPOUNDS;

EID: 0037451410     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390328     Document Type: Article

References (47)

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5. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
6. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
7. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
8. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
9. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
10. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
11. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
12. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
13. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
14. For reviews on asymmetric conjugate additions of alkyl metal compounds to unsaturated carbonyls, see: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196; b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236; c) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold, Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258; for representative recent advances, see: d) X. Hu, H. Chen, X. Zhang, Angew. Chem. 1999, 111, 3720-3723; Angew. Chem. Int. Ed. 1999, 38, 3518-3521; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988-2989; f) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878; g) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879-2888; h) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446; i) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634; j) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359; k) R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702; l) L. A. Arnold, R. Naasz, A. Minaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254; m) L. Liang, T. T. L. An-Yeung, A. S. C. Chan, Org. Lett. 2002, 4, 3799-3801.
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17. a) S. J. Degrado, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 13362-13363;
18. a) S. J. Degrado, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 13362-13363; for a related process involving cyclic nitroalkenes, see: b) C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193.
19. a) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889; for reviews regarding screening strategies for optimal catalyst identification, see: b) M. B. Francis, T. F. Jamison, E. N. Jacobsen, Curr. Opin. Chem. Biol. 1998, 2, 422-428; c) H. B. Kagan, J. Organomet. Chem. 1998, 567, 3-6; d) K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Curr. Opin. Chem. Biol. 1999, 3, 313-319; e) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; f) M. L. Snapper, A. H. Hoveyda, Combinatorial Chemistry (Ed.: H. Fenniri), Oxford University Press, Oxford, 2000, pp. 433-455.
20. a) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889; for reviews regarding screening strategies for optimal catalyst identification, see: b) M. B. Francis, T. F. Jamison, E. N. Jacobsen, Curr. Opin. Chem. Biol. 1998, 2, 422-428; c) H. B. Kagan, J. Organomet. Chem. 1998, 567, 3-6; d) K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Curr. Opin. Chem. Biol. 1999, 3, 313-319; e) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; f) M. L. Snapper, A. H. Hoveyda, Combinatorial Chemistry (Ed.: H. Fenniri), Oxford University Press, Oxford, 2000, pp. 433-455.
21. a) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889; for reviews regarding screening strategies for optimal catalyst identification, see: b) M. B. Francis, T. F. Jamison, E. N. Jacobsen, Curr. Opin. Chem. Biol. 1998, 2, 422-428; c) H. B. Kagan, J. Organomet. Chem. 1998, 567, 3-6; d) K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Curr. Opin. Chem. Biol. 1999, 3, 313-319; e) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; f) M. L. Snapper, A. H. Hoveyda, Combinatorial Chemistry (Ed.: H. Fenniri), Oxford University Press, Oxford, 2000, pp. 433-455.
22. a) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889; for reviews regarding screening strategies for optimal catalyst identification, see: b) M. B. Francis, T. F. Jamison, E. N. Jacobsen, Curr. Opin. Chem. Biol. 1998, 2, 422-428; c) H. B. Kagan, J. Organomet. Chem. 1998, 567, 3-6; d) K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Curr. Opin. Chem. Biol. 1999, 3, 313-319; e) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; f) M. L. Snapper, A. H. Hoveyda, Combinatorial Chemistry (Ed.: H. Fenniri), Oxford University Press, Oxford, 2000, pp. 433-455.
23. a) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889; for reviews regarding screening strategies for optimal catalyst identification, see: b) M. B. Francis, T. F. Jamison, E. N. Jacobsen, Curr. Opin. Chem. Biol. 1998, 2, 422-428; c) H. B. Kagan, J. Organomet. Chem. 1998, 567, 3-6; d) K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Curr. Opin. Chem. Biol. 1999, 3, 313-319; e) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; f) M. L. Snapper, A. H. Hoveyda, Combinatorial Chemistry (Ed.: H. Fenniri), Oxford University Press, Oxford, 2000, pp. 433-455.
24. a) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889; for reviews regarding screening strategies for optimal catalyst identification, see: b) M. B. Francis, T. F. Jamison, E. N. Jacobsen, Curr. Opin. Chem. Biol. 1998, 2, 422-428; c) H. B. Kagan, J. Organomet. Chem. 1998, 567, 3-6; d) K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Curr. Opin. Chem. Biol. 1999, 3, 313-319; e) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; f) M. L. Snapper, A. H. Hoveyda, Combinatorial Chemistry (Ed.: H. Fenniri), Oxford University Press, Oxford, 2000, pp. 433-455.
25. a) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889; for reviews regarding screening strategies for optimal catalyst identification, see: b) M. B. Francis, T. F. Jamison, E. N. Jacobsen, Curr. Opin. Chem. Biol. 1998, 2, 422-428; c) H. B. Kagan, J. Organomet. Chem. 1998, 567, 3-6; d) K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Curr. Opin. Chem. Biol. 1999, 3, 313-319; e) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; f) M. L. Snapper, A. H. Hoveyda, Combinatorial Chemistry (Ed.: H. Fenniri), Oxford University Press, Oxford, 2000, pp. 433-455.
26. For a study on Cu-catalyzed asymmetric conjugate additions to alkylidene malonates, where only low-to-moderate selectivities (5-73% ee) are obtained, see: A. Alexakis, C. Benhaim, Tetrahedron: Asymmetry 2001, 12, 1151-1157.
27. For enantioselective conjugate additions of sterically hindered (tBu and cyclohexyl) radicals to unsaturated N-acyloxazolidinones, see: a) M. P. Sibi, J. Ji, J. H. Wu, S. Gurtler, N. A. Porter, J. Am. Chem. Soc. 1996, 118, 9200-9201; b) M. P. Sibi, J. Ji, J. Org. Chem. 1997, 62, 3800-3801.
28. For enantioselective conjugate additions of sterically hindered (tBu and cyclohexyl) radicals to unsaturated N-acyloxazolidinones, see: a) M. P. Sibi, J. Ji, J. H. Wu, S. Gurtler, N. A. Porter, J. Am. Chem. Soc. 1996, 118, 9200-9201; b) M. P. Sibi, J. Ji, J. Org. Chem. 1997, 62, 3800-3801.
29. Since control experiments showed that with Gly as AA3, the phosphane corresponding to 7 affords less than 20% ee (5a → 6), a new route for synthesis of ligand libraries with nBu termini was developed and utilized. See the Supporting Information for details.
30. See the Supporting Information for details of the screening studies.
31. For example, see: a) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779;
32. For example, see: a) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
33. b) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285;
34. c) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508; Angew. Chem. Int. Ed. 2001, 40, 1456-1460;
35. c) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508; Angew. Chem. Int. Ed. 2001, 40, 1456-1460;
36. d) J. R. Porter, J. F. Traverse, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 984-985;
37. e) H. Deng, M.P. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2002, 114, 1051-1054; Angew. Chem. Int. Ed. 2002, 41, 1009-1012.
38. e) H. Deng, M.P. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2002, 114, 1051-1054; Angew. Chem. Int. Ed. 2002, 41, 1009-1012.
39. a) S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179, and references therein; for applications to catalytic cross-metathesis, see: b) J. Cossy, S. BouzBouz, A. H. Hoveyda, J. Organomet. Chem. 2001, 624, 327-332; c) S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett 2001, 430-432.
40. a) S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179, and references therein; for applications to catalytic cross-metathesis, see: b) J. Cossy, S. BouzBouz, A. H. Hoveyda, J. Organomet. Chem. 2001, 624, 327-332; c) S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett 2001, 430-432.
41. a) S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179, and references therein; for applications to catalytic cross-metathesis, see: b) J. Cossy, S. BouzBouz, A. H. Hoveyda, J. Organomet. Chem. 2001, 624, 327-332; c) S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett 2001, 430-432.
42. 2] affords the opposite enantiomer of 6 in 69% yield and only 64% ee.
43. 2] are carried out at lower temperatures, since transformations performed at 4 °C, which also proceed at a significantly slower pace than other alkyl zinc reagents, lead to the formation of unidentified products.
44. Reactions of various unsaturated dimethyl oxazolidinones corresponding to substrates in Table 2 leads to significantly slower rates of reaction.
45. A. Basha, M. Lipton, S. M. Weinreb, Tetrahedron Lett. 1977, 18, 4171-4172.
46. D. A. Evans, T. C. Britton, J. A. Ellman, Tetrahedron Lett. 1987, 28, 6141-6144.
47. A. H. Hoveyda, Handbook of Combinatorial Chemistry, (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, pp. 991-1016.