Biocatalytic approaches to both enantiomers of (2R*,3S*)-2-allyloxy-3,4,5,6-tetrahydro-2H-pyran-3-ol

Tetrahedron

Volumn 52, Issue 24, 1996, Pages 8123-8134

  Sugai, Takeshi ^a   Ikeda, Hajime ^a   Ohta, Hiromichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BURKHOLDERIA CEPACIA; PSEUDOMONAS;

GLYCOSIDASE; ORGANOMETALLIC COMPOUND; TRIACYLGLYCEROL LIPASE;

ACETYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; DRUG STRUCTURE; ENANTIOMER; OPTICS; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 0029933876     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00374-2     Document Type: Article

References (57)

1. Oppolzer, W. Tetrahedron 1987, 43, 1969-2004; Whitesell, J. K. Chem. Rev. 1992, 92, 953-964;
2. Oppolzer, W. Tetrahedron 1987, 43, 1969-2004; Whitesell, J. K. Chem. Rev. 1992, 92, 953-964;
3. Kunz, H. Pure. Appl. Chem. 1995, 67, 1627-1636.
4. Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Pure Appl. Chem. 1992, 64, 1925-1931; Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Synlett 1993, 81-82; Charette, A. B.; Benslimane, A. F.; Mellon, C. Tetrahedron Lett. 1995, 36, 8557-8560; Charette, A. B.; Mellon, C.; Motamedi, M. Tetrahedron Lett. 1995, 36, 8561-8564.
5. Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Pure Appl. Chem. 1992, 64, 1925-1931; Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Synlett 1993, 81-82; Charette, A. B.; Benslimane, A. F.; Mellon, C. Tetrahedron Lett. 1995, 36, 8557-8560; Charette, A. B.; Mellon, C.; Motamedi, M. Tetrahedron Lett. 1995, 36, 8561-8564.
6. Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Pure Appl. Chem. 1992, 64, 1925-1931; Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Synlett 1993, 81-82; Charette, A. B.; Benslimane, A. F.; Mellon, C. Tetrahedron Lett. 1995, 36, 8557-8560; Charette, A. B.; Mellon, C.; Motamedi, M. Tetrahedron Lett. 1995, 36, 8561-8564.
7. Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Pure Appl. Chem. 1992, 64, 1925-1931; Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Synlett 1993, 81-82; Charette, A. B.; Benslimane, A. F.; Mellon, C. Tetrahedron Lett. 1995, 36, 8557-8560; Charette, A. B.; Mellon, C.; Motamedi, M. Tetrahedron Lett. 1995, 36, 8561-8564.
8. Weisner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985, 68, 300-314; Thiem, J.; Schöttmer, B. Angew. Chem. Int. Ed. Engl. 1987, 26, 555-557; Beau, J.-M.; Jaurand, G.; Esnault, J.; Sinaÿ, P. Tetrahedron Lett. 1987, 28, 1105-1108; Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749; Postema, M. H. D. Tetrahedron 1992, 48, 8455-8599; Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
9. Weisner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985, 68, 300-314; Thiem, J.; Schöttmer, B. Angew. Chem. Int. Ed. Engl. 1987, 26, 555-557; Beau, J.-M.; Jaurand, G.; Esnault, J.; Sinaÿ, P. Tetrahedron Lett. 1987, 28, 1105-1108; Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749; Postema, M. H. D. Tetrahedron 1992, 48, 8455-8599; Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
10. Weisner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985, 68, 300-314; Thiem, J.; Schöttmer, B. Angew. Chem. Int. Ed. Engl. 1987, 26, 555-557; Beau, J.-M.; Jaurand, G.; Esnault, J.; Sinaÿ, P. Tetrahedron Lett. 1987, 28, 1105-1108; Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749; Postema, M. H. D. Tetrahedron 1992, 48, 8455-8599; Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
11. Weisner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985, 68, 300-314; Thiem, J.; Schöttmer, B. Angew. Chem. Int. Ed. Engl. 1987, 26, 555-557; Beau, J.-M.; Jaurand, G.; Esnault, J.; Sinaÿ, P. Tetrahedron Lett. 1987, 28, 1105-1108; Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749; Postema, M. H. D. Tetrahedron 1992, 48, 8455-8599; Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
12. Weisner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985, 68, 300-314; Thiem, J.; Schöttmer, B. Angew. Chem. Int. Ed. Engl. 1987, 26, 555-557; Beau, J.-M.; Jaurand, G.; Esnault, J.; Sinaÿ, P. Tetrahedron Lett. 1987, 28, 1105-1108; Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749; Postema, M. H. D. Tetrahedron 1992, 48, 8455-8599; Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
13. Weisner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985, 68, 300-314; Thiem, J.; Schöttmer, B. Angew. Chem. Int. Ed. Engl. 1987, 26, 555-557; Beau, J.-M.; Jaurand, G.; Esnault, J.; Sinaÿ, P. Tetrahedron Lett. 1987, 28, 1105-1108; Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749; Postema, M. H. D. Tetrahedron 1992, 48, 8455-8599; Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
14. Attempts of the enzyme-catalyzed hydrolysis of glycosidic bond of deoxygenated sugar have been reported: Yamai, M.; Miyake, Y.; Yamashita, T.; Yokomizo, J.; Nishio, T.; Oku, T.; Ito, T. Abstract of Papers, Annual Meeting of Japan Society for Bioscience, Biotechnology, and Agrochemistry, 1994, 68, 518; Nishio, T.; Miyake, Y.; Kubota, K.; Yamai, M.; Miki, S.; Ito, T.; Oku, T. Carbohydr. Res. 1996, 280, 357-363.
15. Attempts of the enzyme-catalyzed hydrolysis of glycosidic bond of deoxygenated sugar have been reported: Yamai, M.; Miyake, Y.; Yamashita, T.; Yokomizo, J.; Nishio, T.; Oku, T.; Ito, T. Abstract of Papers, Annual Meeting of Japan Society for Bioscience, Biotechnology, and Agrochemistry, 1994, 68, 518; Nishio, T.; Miyake, Y.; Kubota, K.; Yamai, M.; Miki, S.; Ito, T.; Oku, T. Carbohydr. Res. 1996, 280, 357-363.
16. Sweet, F.; Brown, R. K. Can. J. Chem. 1966, 44, 1571-1576. Instead of 'allyl glycoside' 1a, an 'ethyl glycoside' 3a was used as the substrate, because a microorganism which hydrolyzes the 'glycosidic' bond was expected to utilize ethanol better than allyl alcohol, as the carbon source for its growth. Allyl alcohol, which will be produced by the hydrolysis of 1a might have a toxic effect as it will form a Michael accepter in the subsequent metabolic pathway.
17. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 54, 2543-2549; Dale, J. A.; Mosher, H. S. J. Am. Chem, Soc. 1973, 95, 512-519.
18. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 54, 2543-2549; Dale, J. A.; Mosher, H. S. J. Am. Chem, Soc. 1973, 95, 512-519.
19. Langrand, G.; Baratti, J.; Buono, G.; Triantaphylides, C. Tetrahedron Lett. 1986, 27, 29-32;
20. Langrand, G.; Secchi, M.; Baratti, J.; Buono, G.; Triantaphylides, C. Tetrahedron Lett. 1986, 27, 1857-1860;
21. Xie, Z.-F.; Nakamura, I.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1988, 966-967;
22. Faber, K.; Hönig, H.; Seufer-Wasserthal, P. Tetrahedron Lett. 1988, 29, 1903-1904;
23. Laumen, K.; Seemayer, R.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1990, 49-51;
24. Whitesell, J. K.; Lawrence, R. M. Org. Synth. 1990, 69, 1-9;
25. Ciuffreda, P.; Colombo, P.; Ronchetti, F.; Toma, L. J. Org. Chem. 1990, 55, 4187-4190;
26. Schwanz, A.; Madan, P.; Meltz, M.; Saccomano, N. A. Tetrahedron Lett. 1992, 33, 1201-1202;
27. Colombo, D.; Ronchetti, F.; Scala, A.; Taino, I. M.; Toma, L. BioMed. Chem. 1993, 1, 375-376;
28. Zarevúcka, M.; Rejzek, M.; Wimmer, Z.; Saman, D.; Streinz, L. Tetrahedron 1993, 49, 5305-5314;
29. Gupta, A. K.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1993, 3, 879-888;
30. Fukazawa, T.; Hashimoto, T. Tetrahedron: Asymmetry 1993, 4, 2323-2326;
31. Ling, L.; Ozaki, S. Tetrahedron Lett. 1993, 34, 2051-2054;
32. Weissfloch, A.; Azerad, D. BioMed. Chem. 1994, 2, 493-500;
33. Takahashi, M.; Ogasawara, K. Tetrahedron: Asymmetry 1995, 6, 1617-1620;
34. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718;
35. Basavaiah, D.; Krishna, P. R.; Bharathi, T. K. Tetrahedron: Asymmetry 1995, 6, 439-454;
36. Basavaiah, D.; Pandiaraju, S.; Muthukumaran, K. Tetrahedron: Asymmetry 1996, 7, 13-16.
37. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499-525; Boland, W.; Frössl, C.; Lorenz, M. Synthesis 1991, 1049-1072; Faber, K.; Riva, S. Synthesis 1992, 895-910; Fang, J.-M.; Wong, C.-H. Synlett 1994, 393-402; Theil, F. Chem. Rev. 1995, 95, 2203-2227; Mori, K. Synlett 1995, 1097-1109.
38. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499-525; Boland, W.; Frössl, C.; Lorenz, M. Synthesis 1991, 1049-1072; Faber, K.; Riva, S. Synthesis 1992, 895-910; Fang, J.-M.; Wong, C.-H. Synlett 1994, 393-402; Theil, F. Chem. Rev. 1995, 95, 2203-2227; Mori, K. Synlett 1995, 1097-1109.
39. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499-525; Boland, W.; Frössl, C.; Lorenz, M. Synthesis 1991, 1049-1072; Faber, K.; Riva, S. Synthesis 1992, 895-910; Fang, J.-M.; Wong, C.-H. Synlett 1994, 393-402; Theil, F. Chem. Rev. 1995, 95, 2203-2227; Mori, K. Synlett 1995, 1097-1109.
40. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499-525; Boland, W.; Frössl, C.; Lorenz, M. Synthesis 1991, 1049-1072; Faber, K.; Riva, S. Synthesis 1992, 895-910; Fang, J.-M.; Wong, C.-H. Synlett 1994, 393-402; Theil, F. Chem. Rev. 1995, 95, 2203-2227; Mori, K. Synlett 1995, 1097-1109.
41. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499-525; Boland, W.; Frössl, C.; Lorenz, M. Synthesis 1991, 1049-1072; Faber, K.; Riva, S. Synthesis 1992, 895-910; Fang, J.-M.; Wong, C.-H. Synlett 1994, 393-402; Theil, F. Chem. Rev. 1995, 95, 2203-2227; Mori, K. Synlett 1995, 1097-1109.
42. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499-525; Boland, W.; Frössl, C.; Lorenz, M. Synthesis 1991, 1049-1072; Faber, K.; Riva, S. Synthesis 1992, 895-910; Fang, J.-M.; Wong, C.-H. Synlett 1994, 393-402; Theil, F. Chem. Rev. 1995, 95, 2203-2227; Mori, K. Synlett 1995, 1097-1109.
43. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
44. A similar inverse enantiomeric preference between Pseudomonas cepacia lipase and Candida cylindracea lipase-catalyzed reaction has been observed: Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 36, 4185-4188.
45. Panda, S.; Dordick, J. S. J. Am. Chem. Soc. 1991, 113, 2253-2259; Terradas, F.; Teston-Henry, M.; Fitzpatrrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 390-396; Herradón, B. J. Org. Chem. 1994, 2891-2893; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1994, 50, 4681-4690; Kvittingen, L. Tetrahedron 1994, 50, 8253-8274; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799-8808; Hansen, T. V.; Waagen, V.; Partali, V.; Anthonsen, T. Tetrahedron: Asymmetry 1995, 6, 499-504.
46. Panda, S.; Dordick, J. S. J. Am. Chem. Soc. 1991, 113, 2253-2259; Terradas, F.; Teston-Henry, M.; Fitzpatrrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 390-396; Herradón, B. J. Org. Chem. 1994, 2891-2893; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1994, 50, 4681-4690; Kvittingen, L. Tetrahedron 1994, 50, 8253-8274; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799-8808; Hansen, T. V.; Waagen, V.; Partali, V.; Anthonsen, T. Tetrahedron: Asymmetry 1995, 6, 499-504.
47. Panda, S.; Dordick, J. S. J. Am. Chem. Soc. 1991, 113, 2253-2259; Terradas, F.; Teston-Henry, M.; Fitzpatrrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 390-396; Herradón, B. J. Org. Chem. 1994, 2891-2893; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1994, 50, 4681-4690; Kvittingen, L. Tetrahedron 1994, 50, 8253-8274; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799-8808; Hansen, T. V.; Waagen, V.; Partali, V.; Anthonsen, T. Tetrahedron: Asymmetry 1995, 6, 499-504.
48. Panda, S.; Dordick, J. S. J. Am. Chem. Soc. 1991, 113, 2253-2259; Terradas, F.; Teston-Henry, M.; Fitzpatrrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 390-396; Herradón, B. J. Org. Chem. 1994, 2891-2893; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1994, 50, 4681-4690; Kvittingen, L. Tetrahedron 1994, 50, 8253-8274; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799-8808; Hansen, T. V.; Waagen, V.; Partali, V.; Anthonsen, T. Tetrahedron: Asymmetry 1995, 6, 499-504.
49. Panda, S.; Dordick, J. S. J. Am. Chem. Soc. 1991, 113, 2253-2259; Terradas, F.; Teston-Henry, M.; Fitzpatrrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 390-396; Herradón, B. J. Org. Chem. 1994, 2891-2893; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1994, 50, 4681-4690; Kvittingen, L. Tetrahedron 1994, 50, 8253-8274; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799-8808; Hansen, T. V.; Waagen, V.; Partali, V.; Anthonsen, T. Tetrahedron: Asymmetry 1995, 6, 499-504.
50. Panda, S.; Dordick, J. S. J. Am. Chem. Soc. 1991, 113, 2253-2259; Terradas, F.; Teston-Henry, M.; Fitzpatrrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 390-396; Herradón, B. J. Org. Chem. 1994, 2891-2893; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1994, 50, 4681-4690; Kvittingen, L. Tetrahedron 1994, 50, 8253-8274; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799-8808; Hansen, T. V.; Waagen, V.; Partali, V.; Anthonsen, T. Tetrahedron: Asymmetry 1995, 6, 499-504.
51. Panda, S.; Dordick, J. S. J. Am. Chem. Soc. 1991, 113, 2253-2259; Terradas, F.; Teston-Henry, M.; Fitzpatrrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 390-396; Herradón, B. J. Org. Chem. 1994, 2891-2893; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1994, 50, 4681-4690; Kvittingen, L. Tetrahedron 1994, 50, 8253-8274; Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799-8808; Hansen, T. V.; Waagen, V.; Partali, V.; Anthonsen, T. Tetrahedron: Asymmetry 1995, 6, 499-504.
52. Larcheveque, M.; Lalande, J. Tetrahedron 1984, 40, 1061-1065.
53. Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643-4647; Kakeya, H.; Sugai, T.; Ohta, H. Agric. Biol. Chem. 1991, 55, 1873-1876; Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813-822; Johnson, C. R.; Xu, Y.; Nicolaou, K. C.; Yang, Z.; Guy, R. K.; Dong, J. G.; Berova, N. Tetrahedron Lett. 1995, 36, 3291-3294.
54. Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643-4647; Kakeya, H.; Sugai, T.; Ohta, H. Agric. Biol. Chem. 1991, 55, 1873-1876; Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813-822; Johnson, C. R.; Xu, Y.; Nicolaou, K. C.; Yang, Z.; Guy, R. K.; Dong, J. G.; Berova, N. Tetrahedron Lett. 1995, 36, 3291-3294.
55. Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643-4647; Kakeya, H.; Sugai, T.; Ohta, H. Agric. Biol. Chem. 1991, 55, 1873-1876; Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813-822; Johnson, C. R.; Xu, Y.; Nicolaou, K. C.; Yang, Z.; Guy, R. K.; Dong, J. G.; Berova, N. Tetrahedron Lett. 1995, 36, 3291-3294.
56. Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643-4647; Kakeya, H.; Sugai, T.; Ohta, H. Agric. Biol. Chem. 1991, 55, 1873-1876; Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813-822; Johnson, C. R.; Xu, Y.; Nicolaou, K. C.; Yang, Z.; Guy, R. K.; Dong, J. G.; Berova, N. Tetrahedron Lett. 1995, 36, 3291-3294.
57. Very recently in a quite independent manner, another type of novel double kinetic resolution has been proposed by Node and co-workers. Starting from a meso-dioxotetracarboxylate, they obtained an enantiomerically enriched form of dioxodicarboxylate by two step enantioselective hydrolysis of ester group with a concomitant spontaneous decarboxylation. See a relating work: Node, M.; Inoue, T.; Araki, M.; Nakamura, D.; Nishide, K. Tetrahedron Lett. 1995, 36, 2255-2256.