Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from L-proline

Tetrahedron

Volumn 67, Issue 48, 2011, Pages 9411-9416

  Hirata, Shigeo ^a   Kuriyama, Masami ^a   Onomura, Osamu ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

(Pyrrolidin 2 yl) phosphonate; Arbusov reaction; Diastereoselective phosphorylation; L Proline

Indexed keywords

(PYRROLIDIN 2 YL)PHOSPHONATE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ARBUSOV REACTION; ARTICLE; CHEMICAL REACTION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 80054863088     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.080     Document Type: Article

References (35)

1. (a) Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassal, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Nature 1978, 272, 56-58;
2. (b) Atherton, F. R.; Hassall, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29-40;
3. (c) Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science 1994, 265, 234-237;
4. (d) Smith, A. B.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879-10888;
5. (e) Alonso, E.; Alonso, E.; Solís, A.; del Pozo, C. Synlett 2000, 698-700.
6. Representative reviews, see: (a) Yokomatsu, T.; Yamaguchi, T.; Shibuya, S. Yuki Gosei Kagaku Kyokaishi 1995, 53, 881-892;
7. (b) Shibuya, S. Yakugaku Zasshi 2004, 124, 725-749;
8. (c) Ordóñez, M.; Rojas-Cabrera, H.; Cativiela, C. Tetrahedron 2009, 65, 17-49.
9. A representative recent review, see: (a) Moonen, K.; Laureyn, I.; Stevens, C. V. Chem. Rev. 2004, 104, 6177-6215;
10. Representative literatures, see: Jacquier, R.; Ouazzani, F.; Roumestant, M.-J.; Viallefont, P. Phosphorus Sulfur 1988, 36, 73-77;
11. (c) Groth, U.; Richter, L.; Schöllkopf, U. Tetrahedron 1992, 48, 117-122;
12. (d) Katritzky, A. R.; Cui, X.-L.; Yang, B.; Steel, P. J. J. Org. Chem. 1999, 64, 1979-1985;
13. (e) Amedjkouh, M.; Westerlund, K. Tetrahedron Lett. 2004, 45, 5175-5177;
14. (f) Kaname, M.; Arakawa, Y.; Yoshifuji, S. Tetrahedron Lett. 2001, 42, 2713-2716;
15. (g) Davis, F. A.; lee, S. H.; Xu, H. J. Org. Chem. 2004, 69, 3774-3781;
16. (h) Wuggenig, F.; Schweifer, A.; Mereiter, K.; Hammerschmidt, F. Eur. J. Org. Chem. 2011, 1870-1879.
17. Onomura, O.; Kirira, P. G.; Tanaka, T.; Tsukada, S. Tetrahedron 2008, 64, 7498-7503.
18. Arbusov reaction of electrochemically prepared N,O-acetal with phosphites: (a) Shono, T.; Matsumura, Y.; Tsubata, K. Tetrahedron Lett. 1981, 22, 3249-3252;
19. (b) Shono, T.; Matsumura, Y.; Tsubata, K.; Uchida, K.; Kanazawa, T.; Tsuda, K. J. Org. Chem. 1984, 49, 3711-3716;
20. (c) Renaud, P.; Seebach, D. Helv. Chim. Acta 1986, 69, 1704-1710.
21. (a) Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.-I.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697-6703;
22. (b) Shono, T.; Matsumura, Y.; Kanazawa, T.; Habuka, M.; Uchida, K.; Toyoda, K. J. Chem. Res., Synop. 1984, 320-321;
23. J. Chem. Res., Miniprint 1984, 2873-2889;
24. (c) Asada, S.; Kato, M.; Asai, K.; Ineyama, T.; Nishi, S.; Izawa, K.; Shono, T. J. Chem. Soc., Chem. Commun. 1989, 486-488;
25. (d) Wong, P. L.; Moeller, K. D. J. Am. Chem. Soc. 1993, 115, 11434-11435;
26. (e) Célimène, C.; Dhimane, H.; Lhommet, G. Tetrahedron 1998, 54, 10457-10468.
27. Recoveries of starting methoxylated compounds caused low yields.
28. In case of N-tert-butoxycarbonylated proline 2d, deprotection of the tert-butoxycarbonyl group occurred.
29. (a) Iwasaki, T.; Horikawa, H.; Matsumoto, K.; Miyoshi, M. J. Org. Chem. 1979, 44, 1552-1554;
30. (b) Shono, T.; Matsumura, Y.; Onomura, O.; Sato, M. J. Org. Chem. 1988, 53, 4118-4121;
31. (c) Matsumura, Y.;Wanyoike, G. N.; Onomura, O.; Maki, T. Electrochim. Acta 2003, 48, 2957-2966;
32. (d) Minato, D.; Mizuta, S.; Kuriyama, M.; Matsumura, Y.; Onomura, O. Tetrahedron 2009, 65, 9742-9748.
33. Diastereoselectivity in these decarboxylative methoxylation was not clear.
34. 3f,h
35. Although similarly 8at was transformed into the corresponding tetraisopropyl ester, its stereochemistry could not be determined.