Catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes [3]

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 10215-10216

  Ji, Jianguo ^a   Barnes, David M ^a   Zhang, Ji ^a   King, Steven A ^a   Wittenberger, Steven J ^a   Morton, Howard E ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMINE; CARBONYL DERIVATIVE; LIGAND; METHYL GROUP; MORPHOLINE DERIVATIVE; NITRO DERIVATIVE; PYRROLIDINE DERIVATIVE; STYRENE DERIVATIVE; WATER;

AMINATION; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; ENANTIOMER; LETTER; STEREOCHEMISTRY;

EID: 0033520797     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992314w     Document Type: Letter

References (34)

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2. For a review of Lewis acid-catalyzed additions of enolate surrogates to electrophiles, see: Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. See also: Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120.
3. For a review of Lewis acid-catalyzed additions of enolate surrogates to electrophiles, see: Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357- 389. See also: Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120.
4. Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references therein.
5. Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452-6453.
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7. (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178.
8. For leading references on Michael additions catalyzed by heterobimetallic complexes, see: (c) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
9. (d) Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557-7558.
10. For an early example of a highly selective catalyzed reaction, see: (a) Cram. D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625-628. For a recent example of a highly selective Mukaiyama Michael reaction, see: (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. For a review of catalyzed conjugate addition reactions, see: (c) Ferigna, B. I.; de Vries, A. H. M. Advances in Catalytic Processes; JAI Press: London, 1995; pp 151-192.
11. For an early example of a highly selective catalyzed reaction, see: (a) Cram. D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625- 628. For a recent example of a highly selective Mukaiyama Michael reaction, see: (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. For a review of catalyzed conjugate addition reactions, see: (c) Ferigna, B. I.; de Vries, A. H. M. Advances in Catalytic Processes; JAI Press: London, 1995; pp 151-192.
12. For an early example of a highly selective catalyzed reaction, see: (a) Cram. D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625- 628. For a recent example of a highly selective Mukaiyama Michael reaction, see: (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. For a review of catalyzed conjugate addition reactions, see: (c) Ferigna, B. I.; de Vries, A. H. M. Advances in Catalytic Processes; JAI Press: London, 1995; pp 151-192.
13. For recent reviews, see: (a) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423-434. (b) Fuji, K.; Node, M. Synlett 1991, 603. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833-847.
14. For recent reviews, see: (a) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423-434. (b) Fuji, K.; Node, M. Synlett 1991, 603. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833-847.
15. For recent reviews, see: (a) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423-434. (b) Fuji, K.; Node, M. Synlett 1991, 603. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833-847.
16. The addition of 1,3-dicarbonyl compounds to nitrostyrene has been reported to be promoted by chiral alkaloid catalysts in up to 43% ee. Brunner, H.; Kimel, B. Monatsh. Chem. 1996, 127, 1063-1072.
17. 2-symmetric bis(oxazoline) ligands in asymmetric catalysis, see: Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
18. 2-symmetric bis(oxazoline) ligands in asymmetric catalysis, see: Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
19. For examples of the use of bis(oxazoline)magnesium complexes in catalysis, see the following. Conjugate additions of O-benzylhydroxylamine to unsaturated amides: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616. Radical additions to α,β-unsaturated imides: (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Diels-Alder reaction: (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074- 3088. (d) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.; Righetti, P. Tetrahedron 1998, 54, 6099-6110. (e) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-7688. (f) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., III. Tetrahedron: Asymmetry 1997, 8, 3079-3087. (g) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810. Nitrone 1,3-dipolar cycloadditions: (h) Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 53, 5483-5488.
20. For examples of the use of bis(oxazoline)magnesium complexes in catalysis, see the following. Conjugate additions of O-benzylhydroxylamine to unsaturated amides: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616. Radical additions to α,β-unsaturated imides: (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Diels-Alder reaction: (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074- 3088. (d) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.; Righetti, P. Tetrahedron 1998, 54, 6099-6110. (e) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-7688. (f) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., III. Tetrahedron: Asymmetry 1997, 8, 3079-3087. (g) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810. Nitrone 1,3-dipolar cycloadditions: (h) Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 53, 5483-5488.
21. For examples of the use of bis(oxazoline)magnesium complexes in catalysis, see the following. Conjugate additions of O-benzylhydroxylamine to unsaturated amides: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616. Radical additions to α,β-unsaturated imides: (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Diels-Alder reaction: (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088. (d) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.; Righetti, P. Tetrahedron 1998, 54, 6099-6110. (e) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-7688. (f) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., III. Tetrahedron: Asymmetry 1997, 8, 3079-3087. (g) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810. Nitrone 1,3-dipolar cycloadditions: (h) Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 53, 5483-5488.
22. For examples of the use of bis(oxazoline)magnesium complexes in catalysis, see the following. Conjugate additions of O-benzylhydroxylamine to unsaturated amides: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616. Radical additions to α,β-unsaturated imides: (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Diels-Alder reaction: (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074- 3088. (d) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.; Righetti, P. Tetrahedron 1998, 54, 6099-6110. (e) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-7688. (f) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., III. Tetrahedron: Asymmetry 1997, 8, 3079-3087. (g) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810. Nitrone 1,3-dipolar cycloadditions: (h) Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 53, 5483-5488.
23. For examples of the use of bis(oxazoline)magnesium complexes in catalysis, see the following. Conjugate additions of O-benzylhydroxylamine to unsaturated amides: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616. Radical additions to α,β-unsaturated imides: (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Diels-Alder reaction: (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074- 3088. (d) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.; Righetti, P. Tetrahedron 1998, 54, 6099-6110. (e) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-7688. (f) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., III. Tetrahedron: Asymmetry 1997, 8, 3079-3087. (g) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810. Nitrone 1,3-dipolar cycloadditions: (h) Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 53, 5483-5488.
24. For examples of the use of bis(oxazoline)magnesium complexes in catalysis, see the following. Conjugate additions of O-benzylhydroxylamine to unsaturated amides: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616. Radical additions to α,β-unsaturated imides: (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Diels-Alder reaction: (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074- 3088. (d) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.; Righetti, P. Tetrahedron 1998, 54, 6099-6110. (e) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-7688. (f) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., III. Tetrahedron: Asymmetry 1997, 8, 3079-3087. (g) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810. Nitrone 1,3-dipolar cycloadditions: (h) Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 53, 5483-5488.
25. For examples of the use of bis(oxazoline)magnesium complexes in catalysis, see the following. Conjugate additions of O-benzylhydroxylamine to unsaturated amides: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616. Radical additions to α,β-unsaturated imides: (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Diels-Alder reaction: (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074- 3088. (d) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.; Righetti, P. Tetrahedron 1998, 54, 6099-6110. (e) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-7688. (f) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., III. Tetrahedron: Asymmetry 1997, 8, 3079-3087. (g) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810. Nitrone 1,3-dipolar cycloadditions: (h) Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 53, 5483-5488.
26. For examples of the use of bis(oxazoline)magnesium complexes in catalysis, see the following. Conjugate additions of O-benzylhydroxylamine to unsaturated amides: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616. Radical additions to α,β-unsaturated imides: (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Diels-Alder reaction: (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074- 3088. (d) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.; Righetti, P. Tetrahedron 1998, 54, 6099-6110. (e) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-7688. (f) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., III. Tetrahedron: Asymmetry 1997, 8, 3079-3087. (g) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810. Nitrone 1,3-dipolar cycloadditions: (h) Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 53, 5483-5488.
27. The adducts of β-ketoesters with nitrostyrenes are formed as 1:1 mixtures of compounds diastereomeric at the product ketoester α-position due to rapid equilibration under the reaction conditions. By NMR, the enol tautomer is also observed sometimes. See Supporting Information.
28. 3 is added, followed by 200 mg of 4-Å molecular sieves, and the resulting mixture is stirred for an additional 90 min. Following this, nitrostyrene (149 mg, 1 mmol, 1 equiv) is added, followed by ethyl acetoacetate (0.15 mL, 1.2 mmol, 1.2 equiv) and N-methylmorpholine (6.6 μL, 0.06 mmol, 0.06 equiv). Conversion and selectivity are determined by HPLC analysis. See the Supporting Information for details.
29. For a computational study of the effect of the bridge substituents on the Diels-Alder reaction catalyzed by bis(oxazoline)copper complexes, see: Davies, I. W.; Deeth, R. J.; Larsen, R. D.; Reider, P. J. Tetrahedron Lett. 1999, 40, 1233-1236. See also ref 9.
30. The effect of water on magnesium bis(oxazoline)-catalyzed reactions has been documented in other cases (refs 10d,e,h). See the Supporting Information for an investigation of this effect.
31. D = -33.8 (c 0.89 MeOH) for the (S)-isomer: Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42).
32. D = -33.8 (c 0.89 MeOH) for the (S)-isomer: Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42).
33. D = -33.8 (c 0.89 MeOH) for the (S)-isomer: Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42).
34. See Supporting Information for a description of possible transition states.