Enantiodivergent Preparation of Optically Active Oxindoles Having a Stereogenic Quaternary Carbon Center at the C3 Position via the Lipase-Catalyzed Desymmetrization Protocol: Effective Use of 2-Furoates for Either Enzymatic Esterification or Hydrolysis

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2478-2486

  Akai, Shuji ^a   Tsujino, Toshiaki ^a   Akiyama, Emi ^a   Tanimoto, Kouichi ^a   Naka, Tadaatsu ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; ENZYMES; ESTERIFICATION; HYDROLYSIS; SOLVENTS; STEREOCHEMISTRY;

DESYMMETRIZATION REACTIONS; ENANTIOSELECTIVITY;

ORGANIC COMPOUNDS;

2 FUROIC ACID DERIVATIVE; CARBON; OXINDOLE; SOLVENT; TRIACYLGLYCEROL LIPASE; WATER;

ARTICLE; CATALYSIS; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS; TRANSESTERIFICATION;

CANDIDA; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; ESTERIFICATION; FURANS; HYDROLYSIS; INDICATORS AND REAGENTS; INDOLES; LIPASE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 1842503938     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035749h     Document Type: Article

References (55)

1. For recent reviews, see: Saxton, J. E. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 51, Chapter 1.
2. Toyota, M.; Ihara, M. Nat. Prod. Rep. 1998, 327-340.
3. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075.
4. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209-2219.
5. For some recent examples of the asymmetric total syntheses of spirotryprostatins, see: Overman, L. E.; Rosen, M. D. Angew. Chem., Int. Ed. 2099, 39, 4596-4599.
6. Bagul, T. D.; Lakshmaiah, G.; Kawabata, T.; Fuji, K. Org. Lett. 2002, 4, 249-251.
7. Meyers, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 694-696.
8. Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135-3137.
9. For recent examples of the asymmetric total synthesis of physostigmine, see: Matsuura, T.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6500-6503.
10. Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675-678.
11. For an example of the asymmetric total synthesis of esermethole, see: Fuji, K.; Kawabata, T.; Ohmori, T.; Shang, M.; Node, M. Heterocycles 1998, 47, 951-964.
12. For some other recent examples, see: (a) Lakshmaiah, G.; Kawabata, T.; Shang, M.; Fuji, K. J. Org. Chem. 1999, 64, 1699-1704.
13. (b) Yokoshima, S.; Tokuyama, H.; Fukuyama T. Angew. Chem., Int. Ed. 2000, 39, 4073-4075.
14. (c) Oestreich, M.; Dennison, P. R.; Kodanko, J. J.; Overman, L. E. Angew. Chem., Int. Ed. 2001, 40, 1439-1442.
15. (d) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921-3924.
16. (e) Takayama, H.; Fujiwara, R.; Kasai, Y.; Kitajima, M.; Aimi, N. Org. Lett. 2003, 5, 2967-2970.
17. For recent reviews, see: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. Bornscheuer, U. T.; Kazlauskas, R. J. In Hydrolases in Organic Synthesis; Wiley: Weinheim, 1999. Theil, F. Tetrahedron 2000, 56, 2905-2919. Faber, K. In Biotransformations in Organic Chemistry, 4th ed.; Springer-Verlag: Berlin, 2000. Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 2001, 1475-1499.
18. For recent reviews, see: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. Bornscheuer, U. T.; Kazlauskas, R. J. In Hydrolases in Organic Synthesis; Wiley: Weinheim, 1999. Theil, F. Tetrahedron 2000, 56, 2905-2919. Faber, K. In Biotransformations in Organic Chemistry, 4th ed.; Springer-Verlag: Berlin, 2000. Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 2001, 1475-1499.
19. For recent reviews, see: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. Bornscheuer, U. T.; Kazlauskas, R. J. In Hydrolases in Organic Synthesis; Wiley: Weinheim, 1999. Theil, F. Tetrahedron 2000, 56, 2905-2919. Faber, K. In Biotransformations in Organic Chemistry, 4th ed.; Springer-Verlag: Berlin, 2000. Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 2001, 1475-1499.
20. For recent reviews, see: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. Bornscheuer, U. T.; Kazlauskas, R. J. In Hydrolases in Organic Synthesis; Wiley: Weinheim, 1999. Theil, F. Tetrahedron 2000, 56, 2905-2919. Faber, K. In Biotransformations in Organic Chemistry, 4th ed.; Springer-Verlag: Berlin, 2000. Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 2001, 1475-1499.
21. For recent reviews, see: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826. Bornscheuer, U. T.; Kazlauskas, R. J. In Hydrolases in Organic Synthesis; Wiley: Weinheim, 1999. Theil, F. Tetrahedron 2000, 56, 2905-2919. Faber, K. In Biotransformations in Organic Chemistry, 4th ed.; Springer-Verlag: Berlin, 2000. Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 2001, 1475-1499.
22. Hanefeld, U. Org. Biomol. Chem. 2003, 1, 2405-2415.
23. Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897-901.
24. Nonenzymatic desymmetrization of the oxindoles or indolines having two identical substituents at the C3 position has never been reported to the best of our knowledge.
25. 2 chromatography, and the subsequent chemical transformations. For migrations on the hydrolysis approaches, see: (a) Crout, D. H. G.; Gaudet, V. S. B.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 808-810.
26. (b) Xie, Z.-F.; Nakamura, I.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1988, 966-967.
27. (c) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C-H. J. Am. Chem. Soc. 1988, 110, 7200-7205.
28. (d) Suemune, H.; Harabe, T.; Xie, Z.-F.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 4337-4344.
29. (e) Liu, K. K.-C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1990, 3, 169-177.
30. (f) Prasad, K.; Estermann, H.; Underwood, R. L.; Chen. C.-P.; Kucerovy, A.; Repic, O. J. Org. Chem. 1995, 60, 7693-7696.
31. (g) Bódai, V.; Novák, L.; Poppe, L. Synlett 1999, 759-761.
32. (h) Egri, G.; Bálint, J.; Peredi, R.; Fogassy, E.; Novák, L.; Poppe, L. J. Mol. Cat. B 2000, 10, 583-596.
33. For migrations on the esterification approaches, see: (i) Nicolosi, G.; Patti, A.; Piattelli, M.; Sanfilippo, C. Tetrahedron: Asymmetry 1994, 5, 283-288.
34. (j) Nicolosi, G.; Patti, A.; Piattelli, M.; Sanfilippo, C. Tetrahedron: Asymmetry 1995, 6, 519-524.
35. (k) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1997, 8, 283-291.
36. (a) Akai, S.; Naka, T.; Fujita, T.; Takebe, Y.; Kita, Y. Chem. Commun. 2000, 1461-1462.
37. (b) Akai, S.; Naka, T.; Fujita, T.; Takebe, Y.; Tsujino, T.; Kita, Y. J. Org. Chem. 2002, 67, 411-419.
38. For synthetic applications, see: (c) Akai, S.; Tsujino, T.; Fukuda, N.; Iio, K.; Takeda, Y.; Kawaguchi, K.; Naka, T.; Higuchi, K.; Kita, Y. Org. Lett. 2001, 3, 4015-4018.
39. Part of this study was reported in a preliminary communication, see: Akai, S.; Tsujino, T.; Naka, T.; Tanimoto, K.; Kita, Y. Tetrahedron Lett. 2001, 42, 7315-7317.
40. Beckett, A. H.; Daisley, R. W.; Walker, J. Tetrahedron 1968, 24, 6093-6109.
41. See also: Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084-12085.
42. Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1991, 56, 4218-4223.
43. Preparation of 7b was carried out at a temperature (65 °C) higher than that in the reported method (Rajeswaran, W. G.; Cohen, L. A. Tetrahedron 1998, 54, 11375-11380) because of the tardy reaction.
44. Crestini, C.; Saladino, R. Synth. Commun. 1994, 24, 2835-2841. For the preparation of N-benzylisatin, see: Singh, R. P.; Majumder, U.; Shreeve, J. M. J. Org. Chem. 2001, 66, 6263-6267.
45. Crestini, C.; Saladino, R. Synth. Commun. 1994, 24, 2835-2841. For the preparation of N-benzylisatin, see: Singh, R. P.; Majumder, U.; Shreeve, J. M. J. Org. Chem. 2001, 66, 6263-6267.
46. For previous examples of bis-hydroxymethylation at the α-position of the ketones, see: Schneider, G.; Wölfling, J.; Hackler, L.; Meskó, E.; Dombi, G. Synthesis 1985, 194-197.
47. 2O and THF at 30 °C: C. rugosa lipases (Amano AY and Roche Diagnostics CHIRAZYME L-3), C. antarctica lipase (Roche Diagnostics CHIRAZYME L-2), Mucor miehei lipase (Roche Diagnostics CHIRAZYME L-9), Pseudomonas aeruginosa lipase (Toyobo LIP), Pseudomonas sp. lipase (Amano AK), Pseudomonas cepacia lipases (Amano AH and PS), porcine pancreas (Amano), and pig liver esterase (Amano).
48. Caution: During the workup of the transesterification reaction of 3, viz., the filtration of the reaction mixture through a Celite pad followed by concentration of the filtrate in vacuo, we occasionally observed the formation of 3-acetoxymethyl-3-(furoyloxymethy)oxindoles in variable yields. This often occurred when we used a large excess of 5 (for instance, 5 equiv), which resulted in decreasing yields of 2. The side-product seemed to be generated by the acetylation of the optically active 2. The remaining 5 was likely to be involved to some degree, although we have not specified the exact factor that induces the undesired reaction. The side-reaction could be suppressed by stirring the above-mentioned filtrate with water for 30 min to decompose 5 and to extract the resultant 2-furoic acid with the aqueous phase (for details, see Experimental Section).
49. Matsugi, M.; Gotanda, K.; Ohira, C.; Suemura, M.; Sano, A.; Kita, Y. J. Org. Chem. 1999, 64, 6928-6930.
50. Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1988, 53, 3641-3642.
51. 3 in MeOH at room temperature caused a significant racemization of 9 (12% ee) probably via the retro-aldol-aldol reaction.10c The use of Dibal-H successfully cleaved the ester bonding of 8 to give 9 (99% ee, 50% yield, 77% yield based on the consumed 8) and the recovered 8 (35% yield).
52. (a) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477-6487.
53. (b) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499.
54. 2 column chromatography.10b
55. 3N for the chromatography was effective to prevent the contamination.