Chiral C2-symmetric Cu(II) complexes as catalysts for enantioselective hetero-Diels-Alder reactions

Angewandte Chemie - International Edition

Volumn 37, Issue 24, 1999, Pages 3372-3375

  Evans, David A ^a   Olhava, Edward J ^a   Johnson, Jeffrey S ^a   Janey, Jacob M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Copper; Cycloadditions Lewis acids; Synthetic methods

Indexed keywords

COPPER COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033521665     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981231)37:24<3372::AID-ANIE3372>3.0.CO;2-K     Document Type: Article

References (37)

1. For a practical synthesis of the (S,S)-tert-butyl-box ligand, see D. A. Evans, G. S. Peterson, J. S. Johnson, D. M. Barnes, K. R. Campos, K. A. Woerpel, J. Org. Chem. 1998, 63, 4541-4544.
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8. f) D. A. Evans, E. A. Shaughnessy, D. M. Barnes, Tetrahedron Lett. 1997, 38, 3193-3194.
9. a) D. A. Evans, J. A. Murry, M. C. Kozlowski, J. Am. Chem. Soc. 1996, 118, 5814-5815;
10. b) D. A. Evans, M. C. Kozlowski, C. S. Burgey, D. W. C. MacMillan, J. Am. Chem. Soc. 1997, 119, 7893-7894.
11. D. A. Evans, C. S. Burgey, N. A. Paras, T. Vojkovsky, S. W. Tregay, J. Am. Chem. Soc. 1998, 120, 5824-5825.
12. D. A. Evans, J. S. Johnson, J. Am. Chem. Soc. 1998, 120, 4895-4896.
13. Formal hetero-Diels-Alder reactions between electron-rich dienes and pyruvate have been reported with these complexes: a) M. Johannsen, K. A. Jorgensen, Chem. Commun. 1997, 119, 7893-7894; b) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, K. A. Jørgensen, J. Am. Chem. Soc. 1998, 120, 8599-8609.
14. Formal hetero-Diels-Alder reactions between electron-rich dienes and pyruvate have been reported with these complexes: a) M. Johannsen, K. A. Jorgensen, Chem. Commun. 1997, 119, 7893-7894; b) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, K. A. Jørgensen, J. Am. Chem. Soc. 1998, 120, 8599-8609.
15. Auxilary- or catalyst-controlled asymmetric hetero-Diels-Alder reactions of α,β-unsaturated carbonyl compounds with enol ethers: a) G. Dujardin, S. Rossignol, E. Brown, Synthesis 1998, 763-770; b) K. J. McRae, M. A. Rizzacasa, J. Org. Chem. 1997, 62, 1196-1197; c) E. Wada, W. Pei, H. Yasuoka, U. Chin, S. Kanemasa, Tetrahedron 1996, 52, 1205-1220, and references therein; d) L.-E Tietze, C. Schneider, A. Grote, Chem. Eur. J. 1996, 2, 139-148, and references therein; e) L. D. Gaudenzi, S. Apparao, R. R. Schmidt, Tetrahedron 1990, 46, 277-290, and references therein.
16. Auxilary- or catalyst-controlled asymmetric hetero-Diels-Alder reactions of α,β-unsaturated carbonyl compounds with enol ethers: a) G. Dujardin, S. Rossignol, E. Brown, Synthesis 1998, 763-770; b) K. J. McRae, M. A. Rizzacasa, J. Org. Chem. 1997, 62, 1196-1197; c) E. Wada, W. Pei, H. Yasuoka, U. Chin, S. Kanemasa, Tetrahedron 1996, 52, 1205-1220, and references therein; d) L.-E Tietze, C. Schneider, A. Grote, Chem. Eur. J. 1996, 2, 139-148, and references therein; e) L. D. Gaudenzi, S. Apparao, R. R. Schmidt, Tetrahedron 1990, 46, 277-290, and references therein.
17. Auxilary- or catalyst-controlled asymmetric hetero-Diels-Alder reactions of α,β-unsaturated carbonyl compounds with enol ethers: a) G. Dujardin, S. Rossignol, E. Brown, Synthesis 1998, 763-770; b) K. J. McRae, M. A. Rizzacasa, J. Org. Chem. 1997, 62, 1196-1197; c) E. Wada, W. Pei, H. Yasuoka, U. Chin, S. Kanemasa, Tetrahedron 1996, 52, 1205-1220, and references therein; d) L.-E Tietze, C. Schneider, A. Grote, Chem. Eur. J. 1996, 2, 139-148, and references therein; e) L. D. Gaudenzi, S. Apparao, R. R. Schmidt, Tetrahedron 1990, 46, 277-290, and references therein.
18. Auxilary- or catalyst-controlled asymmetric hetero-Diels-Alder reactions of α,β-unsaturated carbonyl compounds with enol ethers: a) G. Dujardin, S. Rossignol, E. Brown, Synthesis 1998, 763-770; b) K. J. McRae, M. A. Rizzacasa, J. Org. Chem. 1997, 62, 1196-1197; c) E. Wada, W. Pei, H. Yasuoka, U. Chin, S. Kanemasa, Tetrahedron 1996, 52, 1205-1220, and references therein; d) L.-E Tietze, C. Schneider, A. Grote, Chem. Eur. J. 1996, 2, 139-148, and references therein; e) L. D. Gaudenzi, S. Apparao, R. R. Schmidt, Tetrahedron 1990, 46, 277-290, and references therein.
19. Auxilary- or catalyst-controlled asymmetric hetero-Diels-Alder reactions of α,β-unsaturated carbonyl compounds with enol ethers: a) G. Dujardin, S. Rossignol, E. Brown, Synthesis 1998, 763-770; b) K. J. McRae, M. A. Rizzacasa, J. Org. Chem. 1997, 62, 1196-1197; c) E. Wada, W. Pei, H. Yasuoka, U. Chin, S. Kanemasa, Tetrahedron 1996, 52, 1205-1220, and references therein; d) L.-E Tietze, C. Schneider, A. Grote, Chem. Eur. J. 1996, 2, 139-148, and references therein; e) L. D. Gaudenzi, S. Apparao, R. R. Schmidt, Tetrahedron 1990, 46, 277-290, and references therein.
20. For general references on the hetero-Diels-Alder reaction, see a) D. L. Boger in Comprehensive Organic Synthesis, Vol. 5 (Eds. : B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, pp. 451-512; b) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987.
21. For general references on the hetero-Diels-Alder reaction, see a) D. L. Boger in Comprehensive Organic Synthesis, Vol. 5 (Eds. : B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, pp. 451-512; b) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987.
22. J. Thorhauge, M. Johannsen, K. A. Jprgensen, Angew. Chem. 1998, 110, 2543-2546; Angew. Chem. Int. Ed. 1998, 37, 2404-2406. Absolute stereochemical assignments of the reaction products were not made in this investigation.
23. J. Thorhauge, M. Johannsen, K. A. Jprgensen, Angew. Chem. 1998, 110, 2543-2546; Angew. Chem. Int. Ed. 1998, 37, 2404-2406. Absolute stereochemical assignments of the reaction products were not made in this investigation.
24. Substrates 4a-c were prepared by an aldol-elimination protocol: H. Sugimura, K. Yoshida, Bull. Chem. Soc. Jpn. 1992, 65, 3209-3211. Substrates 4d-c were prepared by reaction of ethyl vinyl ether or methyl vinyl ether with ethyl chlorooxoacetate: L.-F. Tietze, H. Meier, E. Voss, Synthesis 1988, 274-277 . Substrate 4f was prepared from 4e and phenylmethanethiol in the presence of catalytic amounts of sodium bisulfate. Substrate 4g was prepared by addition of 1-propenylmagnesium bromide to the bis(Weinreb amide) of oxalic acid: M. P. Sibi, M. Marvin, R. Sharma, J. Org. Chem. 1995, 60, 5016-5023. Details of the synthesis of these substrates will appear in a full account of this work.
25. Substrates 4a-c were prepared by an aldol-elimination protocol: H. Sugimura, K. Yoshida, Bull. Chem. Soc. Jpn. 1992, 65, 3209-3211. Substrates 4d-c were prepared by reaction of ethyl vinyl ether or methyl vinyl ether with ethyl chlorooxoacetate: L.-F. Tietze, H. Meier, E. Voss, Synthesis 1988, 274-277 . Substrate 4f was prepared from 4e and phenylmethanethiol in the presence of catalytic amounts of sodium bisulfate. Substrate 4g was prepared by addition of 1-propenylmagnesium bromide to the bis(Weinreb amide) of oxalic acid: M. P. Sibi, M. Marvin, R. Sharma, J. Org. Chem. 1995, 60, 5016-5023. Details of the synthesis of these substrates will appear in a full account of this work.
26. Substrates 4a-c were prepared by an aldol-elimination protocol: H. Sugimura, K. Yoshida, Bull. Chem. Soc. Jpn. 1992, 65, 3209-3211. Substrates 4d-c were prepared by reaction of ethyl vinyl ether or methyl vinyl ether with ethyl chlorooxoacetate: L.-F. Tietze, H. Meier, E. Voss, Synthesis 1988, 274-277 . Substrate 4f was prepared from 4e and phenylmethanethiol in the presence of catalytic amounts of sodium bisulfate. Substrate 4g was prepared by addition of 1-propenylmagnesium bromide to the bis(Weinreb amide) of oxalic acid: M. P. Sibi, M. Marvin, R. Sharma, J. Org. Chem. 1995, 60, 5016-5023. Details of the synthesis of these substrates will appear in a full account of this work.
27. The use of bis(aquo) complex 3 without molecular sieves severely attenuated reactivity, indicating that the anhydrous complex 1 is generated in the presence of moleclar sieves (3 Å).
28. At -40°C: >99% ee; at -20°C: 98% ee; at 0°C: 97% ee; at 25°C: 94% ee.
29. For reviews on the synthetic utility of the Weinreb amide, see a) M. Mentzel, M. R. Hoffman, J. Prakt. Chem. 1997, 339, 517-524; b) M. P. Sibi, Org. Prep. Proced. Int. 1993, 25, 15-40.
30. For reviews on the synthetic utility of the Weinreb amide, see a) M. Mentzel, M. R. Hoffman, J. Prakt. Chem. 1997, 339, 517-524; b) M. P. Sibi, Org. Prep. Proced. Int. 1993, 25, 15-40.
31. 4OH) and chromatographic separation of the adduct and ligand.
32. For an example of catalyst recycling in an enantioselective reaction, see K. B. Hansen, J. L. Leighton, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 10924-10925.
33. 3), lower enantioselectivity and/or reactivity is observed. Attempts to optimize this process and identify the role of the adsorbent are currently being actively studied.
34. D = +14.7° (3R); C-H. R. King, C. D. Poulter, J. Am. Chem. Soc. 1982, 104, 1413).
35. D = +14.7° (3R); C-H. R. King, C. D. Poulter, J. Am. Chem. Soc. 1982, 104, 1413).
36. D = +14.7° (3R); C-H. R. King, C. D. Poulter, J. Am. Chem. Soc. 1982, 104, 1413).
37. D = +14.7° (3R); C-H. R. King, C. D. Poulter, J. Am. Chem. Soc. 1982, 104, 1413).