Highly diastereoselective alkylation of vicinal dianions of chiral succinic acid derivatives: A new general strategy to (R)-β-arylmethyl-γ- butyrolactones

Tetrahedron Letters

Volumn 45, Issue 22, 2004, Pages 4315-4318

  Pohmakotr, Manat ^a   Soorukram, Darunee ^a   Tuchinda, Patoomratana ^a   Prabpai, Samran ^a   Kongsaeree, Palangpon ^a   Reutrakul, Vichai ^a  

^a Mahidol University   (Thailand)

Author keywords

butyrolactone; Chiral succinic acid; Vicinal dianion

Indexed keywords

1,4 BIS(3,4 DIMETHYL 2 OXO 5 PHENYLIMIDAZOLIDIN 1 YL)BUTANE 1,4 DIONE; ANION; BUTYROLACTONE; LACTONE DERIVATIVE; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; METHYLATION; STEREOCHEMISTRY;

EID: 2342498603     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.008     Document Type: Article

References (40)

1. Ayres D.C., Loike J.D. Lignans: Chemical, Biological and Clinical Properties. 1990;Cambridge University Press, Cambridge
2. Ward R.S. Nat. Prod. Rep. 16:1999;75-96
3. For examples, see: Csa'ky A.G., Plumet J. Chem. Soc. Rev. 30:2001;313-320
4. Sibi M.P., Liu P., Ji J., Hajra S., Chen J. J. Org. Chem. 67:2002;1738-1745
5. Sibi M.P., Hasegawa H. Org. Lett. 4:2002;3347-3349
6. Langer T., Illich M., Helmchen G. Synlett. 1996;1137-1139
7. Beckett R.P., Crimmin M.J., Davis M.H., Spavold Z. Synlett. 1993;137-138
8. Pohmakotr M., Sampaongoen L., Issaree A., Tuchinda P., Reutrakul V. Tetrahedron Lett. 44:2003;6717-6720;
9. Pohmakotr M., Issaree A., Sampaongoen L., Tuchinda P., Reutrakul V. Tetrahedron Lett. 44:2003;7937-7940
10. Syntheses based on vicinal anion of (-)-dimenthyl succinate, see: Lee E., Choi S.-J., Kim H., Han H.-O., Kim Y.-K., Min S.-I., Son S.-H., Lim S.-M., Jang W.-S. Angew. Chem., Int. Ed. 41:2002;176-179
11. Kende A.S., Fujii Y., Mendoza J.S. J. Am. Chem. Soc. 112:1990;9645-9646
12. Misumi A., Iwanaga K., Furuta K., Yamamoto H. J. Am. Chem. Soc. 107:1985;3343-3345
13. Bolm C., Palazzi C., Francio G., Leitner W. Chem. Commun. 2002;1588-1589
14. Doyle M.P., Hu W., Valenzuela M.V. J. Org. Chem. 67:2002;2954-2959. and references cited therein
15. Caro Y., Masaguer C.F., Ravina E. Tetrahedron: Asymmetry. 12:2001;1723-1726
16. Takekawa Y., Shishido K. J. Org. Chem. 66:2001;8490-8503
17. Kamlage S., Sefkow M., Zimmermann N., Peter M.G. Synlett. 2002;77-80
18. Kamlage S., Sefkow M., Pool-Zobel B.L., Peter M.G. Chem. Commun. 2001;331-332
19. Sibi M.P., Liu P., Johnson M.D. Can. J. Chem. 78:2000;133-138
20. Chenevert R., Mohammadi-Ziarani G., Caron D., Dasser M. Can. J. Chem. 77:1999;223-226
21. Brinksma J., Deen H.V.D., Oeveren A.V., Feringa B.L. J. Chem. Soc., Perkin Trans. 1. 1998;4159-4163
22. Charlton J.L., Chee G. Can. J. Chem. 75:1997;1076-1083
23. Gagnon R., Gagnon G., Groussain E., Pedragosa-Moreau S., Richardson P.F., Roberts S.M., Willetts A.J., Alphand V., Letreton J., Furstoss R. J. Chem. Soc., Perkin Trans. 1. 1995;2527-2528
24. Lemoult S.C., Richardson P.F., Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 1995;89-91
25. Itoh T., Chika J., Takagi Y., Nishiyama S. J. Org. Chem. 58:1993;5717-5723
26. Morimoto T., Chiba M., Achiwa K. Tetrahedron. 49:1993;1793-1806
27. Koch S.S.C., Chamberlin A.R. J. Org. Chem. 58:1993;2725-2737
28. Filho H.C.A., Filho U.F.L., Pinheiro S., Vasconcellos M.L.A.A., Costa P.R.R. Tetrahedron: Asymmetry. 5:1994;1219-1220
29. Takano S., Ohashi K., Sugihara T., Ogasawara K. Chem. Lett. 1991;203-206
30. Morimoto T., Chiba M., Achiwa K. Tetrahedron Lett. 31:1990;261-264
31. Morimoto T., Chiba M., Achiwa K. Heterocycles. 30:1990;363-366
32. Shao L., Miyata S., Muramatsu H., Kawano H., Ishii Y., Saburi M., Uchida Y. J. Chem. Soc., Perkin Trans. 1. 1990;1441-1445
33. Yoda H., Kitayama H., Katagiri T., Takabe K. Tetrahedron. 48:1990;3313-3322
34. Treatment of 1a with 1 equiv of LDA, followed by reacting with 1 or 2 equiv of benzyl bromide under the standard conditions provided a low yield of the expected product 3a
35. 1H NMR and MS. In spite of these results, it was still assumed that the vicinal dianion 2a was generated under the conditions described. This may be due to a strong H-bonded complex between diisopropylamine and the dilithiated derivative. Such interaction effecting incomplete deuteration of the generated lithium derivative was reported by Seebach (Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta, 1985, 68, 1373-1393). The reaction of the vicinal dianion 2a with 2.2 equiv of benzyl bromide at -78°C to room temperature overnight (12-16 h) afforded dibenzylated product 9 in 20-30% yields together with 30-40% yields of the chiral auxiliary, (4S, 5R)-(+)-1, 5-dimethyl-4-phenyl-2-imidazolidinone and compound 11. The formation of 9 supported the presence of the vicinal dianion 2a. Compound 9 was obtained as a single diastereomer and its structure is proposed as shown below. The results also indicated that the vicinal dianion 2a slowly decomposed during warming from -78°C to rt to provide 10 and 11.
36. 25 -27 ( c 2, EtOAc); Cohen S.G., Milovanovic A. J. Am. Chem. Soc. 90:1968;3495-3502
37. 2 using SHELXL-97 to give a final R -factor of 0.0493 and wR=0.1130 (all data). Atomic coordinates, bond lengths, bond angles, and thermal parameters have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, ENGLAND (CCDC 216625)
38. Kise N., Ueda T., Kumuda K., Terao Y., Ueda N. J. Org. Chem. 65:2000;464-468. and references cited therein
39. The chiral auxillary was recovered in 85-95% yields and could be reused without loss of diastereoselectivity
40. 3)