Erythro-selective aldol-type reaction of N-sulfonylaldimines with methyl isocyanoacetate catalyzed by gold(I)

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4969-4972

  Hayashi, Tamio ^a   Kishi, Eiji ^a   Soloshonok, Vadim A ^a   Uozumi, Yasuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIAMINO ACID; GOLD; IMINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROLYSIS; ISOMER; STEREOCHEMISTRY;

EID: 0030575363     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00981-1     Document Type: Article

References (35)

1. 1. For reviews on the aldol reaction of isocyanocarboxylates: (a) Hoppe, D. Angew. Chem. Int. Ed. Engl. 1974, 13, 789-804.
2. (b) Matsumoto, K.; Moriya, T.; Suzuki, M. J. Synth. Org. Chem., Jpn. 1985, 43, 764-776.
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4. (b) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J. Org. Chem. 1971, 36, 3316-3323.
5. 3. (a) Soloshonok, V. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245-254.
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11. (g) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235-238.
12. (h) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215-6218.
13. (i) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406.
14. 4. (a) Pastor, S. D.; Kesselring, R.; Togni, A. J. Organomet. Chem. 1992, 429, 415-420.
15. (b) Pastor, S. D.; Togni, A. Helv. Chim. Acta 1991, 74, 905-933.
16. (c) Togni, A.; Blumer, R. E.; Pregosin, P. S. Helv. Chim. Acta 1991, 74, 1533-1543.
17. (d) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649-1664.
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19. (f) Togni, A.; Pastor, S. D. Tetrahedron Lett. 1989, 30, 1071-1072.
20. (g) Togni, A.; Pastor, S. D.; Rihs, G. Helv. Chim. Acta 1989, 72, 1471-1478.
21. (h) Pastor, S. D.; Togni, A. J. Am. Chem. Soc. 1989, 111, 2333-2334.
22. 5. (a) Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron Lett. 1991, 32, 2799-2802.
23. (b) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935-5936.
24. 6. Reaction of α-metalated isocyanide with imines has been reported: Meyer, R.; Schöllkopf, U.; Böhme, P. Liebigs Ann. Chem. 1977, 1183-1193.
25. 7. Bonati, F.; Minghetti, G. Gazz. Chim. Ital. 1973, 103, 373-386.
26. 8. Transition metal-catalyzed aldol-type reaction of imines has been reported: (a) Shida, N.; Kubota, Y.; Fukui, H.; Asao, N.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5023-5026.
27. (b) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161-3162.
28. 9. (a) Love, B. E.; Raje, P. S.; Williams II, T. C. Synlett 1994, 493-494.
29. (b) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777-4780.
30. (c) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468-6470.
31. 10. Under similar reaction conditions (at 40 °C, 1 mol % AuCl(c-HexNC) in MeCN), benzaldehyde gave trans-oxazolinecarboxylate predominantly (cis/trans = 30/70).
32. 3) for cis-imidazolines 2 are as follows: cis-2a: δ 2.38 (s, 3 H), 3.14 (s, 3 H), 5.15 (d, J = 11.6 Hz, 1 H), 5.22 (dd, J = 11.6, 2.0 Hz, 1 H), 6.99 (d, J = 8.3 Hz, 2 H), 7.08-7.22 (m, 5 H), 7.41 (d, J = 8.3 Hz, 2 H), 7.77 (d, J = 2.0 Hz, 1 H). cis-2b: δ 2.40 (s, 3 H), 3.20 (s, 3 H), 5.14 (d, J = 11.6 Hz, 1 H), 5.21 (dd, J = 11.6, 2.0 Hz, 1 H), 6.81 (t, J = 8.6 Hz, 2 H), 6.95-7.02 (m, 2 H), 7.18 (d, J = 8.3 Hz, 2 H), 7.42 (d. J = 8.3 Hz, 2 H), 7.77 (d. J = 2.0 Hz, 1H). cis-2c: δ 2.39 (s, 3 H), 3.21 (s, 3 H), 3.74 (s, 3 H), 5.12 (d, J = 11.2 Hz, 1 H), 5.19 (dd, J = 11.2, 2.0 Hz, 1 H), 6.62 (d, J = 8.6 Hz, 2 H), 6.90 (d, J = 8.6 Hz, 2 H), 7.14 (d, J = 8.3 Hz, 2 H), 7.40 (d, J = 8.3 Hz, 2 H), 7.76 (d, J = 2.0 Hz, 1 H). cis-2d: δ 2.40 (s, 3 H), 3.30 (s, 3 H), 5.09 (d, J = 11.2 Hz, 1 H), 5.18 (dd, J = 11.2, 2.3 Hz, 1 H), 5.85 (d, J = 1.3 Hz, 1 H), 5.89 (d, J = 1.3 Hz, 1 H), 6.34 (d, J = 1.7 Hz, 1 H), 6.55 (dd, J = 8.3, 1.7 Hz, 1 H), 6.59 (d, J = 8.3 Hz, 1 H), 7.18 (d, J = 8.6 Hz, 2 H), 7.44 (d, J = 8.6 Hz, 2 H), 7.75 (d, J = 2.3 Hz, 1 H). cis-2e: δ 2.33 (s, 3 H), 3.58 (s, 3 H), 4.82 (dd, J = 10.9, 9.2 Hz, 1 H), 5.04 (dd, J = 10.9, 2.3 Hz, 1 H), 5.54 (dd, J = 15.8 Hz, 9.2 Hz, 1 H), 6.52 (d, J = 15.8 Hz, 1 H), 7.07-7.12 (m, 3 H), 7.15 (d. J = 8.3 Hz, 2 H), 7.21-7.28 (m, 2 H), 7.64 (d, J = 8.3 Hz, 2 H), 7.67 (d, J = 2.3 Hz, 1 H).
33. 3OD) for α,β-diamino acids 4 and esters 5 are as follows: erythro-4a: δ 2.34 (s, 3 H), 4.39 (d, J = 5.3 Hz, 1 H), 4.76 (d, J = 5.3 Hz, 1 H), 7.10-7.25 (m, 7 H), 7.60 (d, J = 8.3 Hz, 2 H). erythro-5a: δ 2.31 (s, 3 H), 3.75 (s, 3 H), 4.39 (d, J = 6.3 Hz, 1 H), 4.71 (d, J = 6.3 Hz, 1 H), 7.07-7.23 (m, 7 H), 7.54 (d, J = 8.3 Hz, 2 H). threo-4a: δ 2.30 (s, 3 H), 4.14 (d, J = 8.9 Hz, 1 H), 4.68 (d, J = 8.9 Hz, 1 H), 6.99-7.18 (m, 7 H), 7.47 (d, J = 8.3 Hz, 2 H). threo-5a: δ 2.28 (s, 3 H), 3.44 (s, 3 H), 4.24 (d, J = 8.9 Hz, 1 H), 4.68 (d, J = 8.9 Hz, 1 H), 6.99 (d, J = 8.3 Hz, 2 H), 7.06-7.19 (m, 5 H), 7.47 (d, J = 8.3 Hz, 2 H).
34. 3) for trans-imidazolines 2 are as follows: trans-2a: δ 2.39 (s, 3 H), 3.70 (s, 3 H), 4.66 (dd, J = 7.6, 2.3 Hz, 1 H), 5.08 (d, J = 7.6 Hz, 1 H), 7.15-7.27 (m, 7 H), 7.46 (d, J = 8.3 Hz, 2 H), 7.65 (d, J = 2.3 Hz, 1 H). trans-2b: δ 2.42 (s, 3 H), 3.71 (s, 3 H), 4.63 (dd, J = 7.6, 2.0 Hz, 1 H), 5.06 (d, J = 7.6 Hz, 1 H), 6.93 (t, J = 8.6 Hz, 2 H), 7.02-7.18 (m, 2 H), 7.22 (d, J = 8.3 Hz, 2 H), 7.48 (d, J = 8.3 Hz, 2 H), 7.64 (d, J = 2.0 Hz, 1 H). trans-2c: δ 2.40 (s, 3 H), 3.70 (s, 3 H), 3.78 (s, 3 H), 4.65 (dd, J = 7.6, 2.0 Hz, 1 H), 5.04 (d, J = 7.6 Hz, 1 H), 6.75 (d, J = 8.9 Hz, 2 H), 7.06 (d, J = 8.9 Hz, 2 H), 7.19 (d, J = 8.3 Hz, 2 H), 7.45 (d, J = 8.3 Hz, 2 H), 7.64 (d, J = 2.0 Hz, 1 H). trans-2d: δ 2.41 (s, 3 H), 3.70 (s, 3 H), 4.62 (dd, J = 7.6, 1.7 Hz, 1 H), 5.00 (d, J = 7.6 Hz, 1 H), 5.89 (t, J = 1.0 Hz, 1 H), 5.92 (t, J = 1.0 Hz, 1 H), 6.49 (s, 1 H), 6.68 (s, 2 H), 7.22 (d, J = 8.3 Hz. 2 H). 7.49 (d, J = 8.3 Hz, 2 H), 7.63 (d, J = 1.7 Hz, 1 H). trans-2e: δ 2.39 (s, 3 H), 3.73 (s, 3 H), 4.55 (dd, J = 7.6, 2.3 Hz, 1 H), 4.74 (dd, J = 8.3, 7.6 Hz, 1 H), 5.83 (dd, J = 15.8 Hz, 8.3 Hz, 1 H), 6.60 (d, J = 15.8 Hz, 1 H), 7.21-7.33 (m, 7 H), 7.58 (d, J = 2.3 Hz, 1 H), 7.68 (d, J = 8.2 Hz, 2 H).
35. 14. Base-catalyzed isomerization of an oxazolinecarboxylate has been reported: Matsumoto, K.; Ozaki, Y.; Suzuki, M.; Miyoshi, M. Agric. Biol. Chem. 1976, 40, 2045-2050. See also ref 3i.