Practical syntheses of both enantiomers of cyclopropylglycine and of methyl 2-cyclopropyl-2-N-Boc-iminoacetate

Advanced Synthesis and Catalysis

Volumn 348, Issue 9, 2006, Pages 1071-1078

  Larionov, Oleg V ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Amino acids; Cyclopropanes; Enantiomeric resolution; Enzymes; Furans; Small rings

Indexed keywords

EID: 33745711893     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606038     Document Type: Article

References (40)

1. Part 126 in the series "Cyclopropyl Building Blocks for Organic Synthesis"; for part 125 see: M. Marradi, A. Brandi, A. de Meijere, Synlett 2006, 1125-1127;
2. part 124: S. Dalai, V. N. Belov, S. Nizamov, K. Rauch, D. Finsinger, A. de Meijere, Eur. J. Org. Chem. 2006, 2753-2765.
3. A. de Meijere, S. I. Kozhushkov, L. P. Hadjiarapoglou. Topics Curr. Chem. 2000, 149-227, and references cited therein.
4. a) F. Seyed-Mahdavi, S. Teichmann, A. de Meijere, Tetrahedron Lett. 1986, 27, 6185-6188;
5. b) A. de Meijere, S. Teichmann, F. Seyed-Mahdavi, S. Kohlstruk, Liebigs Ann. 1996, 1989-2000.
6. M. Limbach, S. Dalai, A. de Meijere, Adv. Synth. Catal. 2004, 346, 760-766.
7. V. N. Belov, C. Funke, T. Labahn, M. Es-Sayed, A. de Meijere, Eur. J. Org. Chem. 1999, 1345-1356.
8. A. Esposito, P. P. Piras, D. Ramazzotti, M. Taddei, Org. Lett. 2001, 3, 3273-3275.
9. H. K. Chenault, J. Dahmer, G. M. Whitesides, J. Am. Chem. Soc. 1989, 111, 6354-6364.
10. S. I. Kozhushkov, M. Brandi, D. S. Yufit, R. Machinek, A. de Meijere, Liebigs Ann. Recl. 1997, 2197-2204.
11. D. E. Slaughter, R. Subramanian, M. E. Fraley, T. Prueksaritanont, H. Shu, WO Patent 2004 087 050 A2, 2004.
12. Two successful examples for the selective reduction of the functional groups next to hydrogenolytically labile cyclopropane rings with zinc under acidic conditions have recently been described: a) R. P. Wurz, A. B. Charette, J. Org. Chem. 2004, 69, 1262-1269;
13. b) O. V. Larionov, A. de Meijere, Org. Lett. 2004, 6, 2153-2156.
14. a) M. Sypniewski, B. Peke, L. Simon, J. River, J. Org. Chem. 2000, 65, 6595-6600;
15. b) T. Miyazawa, H. Iwanaga, T. Yamada, S. Kuwata, Biotech. Lett. 1994, 16, 373-378;
16. c) T. Miyazawa, H. Iwanaga, T. Yamada, S. Kuwata, Peptide Chem. 1991, 28, 57-60;
17. d) J. L. Moriniere, B. Danree, J. Lemoine, A. Guy, Synth. Commun. 1988, 18, 441-444;
18. e) J. L. Abernethy, R. Bobeck, A. Ledesma, R. Kemp, J. Org. Chem. 1973, 38, 1286-1291.
19. K. O. Hallinan, D. H. G. Crout, W. Errington, J. Chem. Soc., Perkin Trans, 1 1994, 3537-3543.
20. [12].
21. O. V. Larionov, T. F. Savel'eva, K. A. Kochetkov, N. S. Ikonnikov, S. I. Kozhushkov, D. S. Yufit, J. A. K. Howard, V. N. Khrustalev, Yu. N. Belokon, A. de Meijere, Eur. J. Org. Chem. 2003, 869-877.
22. O. V. Larionov, S. I. Kozhushkov, A. de Meijere, Synthesis 2003, 12, 1916-1919.
23. R. S. Coleman A. J. Carpenter, J. Org. Chem. 1993, 58, 4452-4461.
24. a) H. Poisel, U. Schmidt, Angew. Chem. 1976, 9, 295-297;
25. Angew. Chem. Int. Ed. Engl. 1976, 15, 294-296;
26. b) H. Poisel, Chem. Ber. 1975, 108, 2547-2553;
27. c) A. J. Kolar, R. K. Olsen, Synthesis 1977, 457-459.
28. -1 than the cyclopropylideneacetate. Thus, after elimination of HCl from the N-chloro derivative 12, the system arrives at the thermodynamically more stable tautomer.
29. a) Y-R. Luo, J. L. Holmes, J. Phys. Chem. 1992, 96, 9568-9571;
30. b) R. B. Turner, P. Goebel, B. J. Mallon, W. von E. Doering, J. F. Coburn, M. Pomerantz, J. Am. Chem. Soc. 1968, 90, 4315-4322.
31. See, for example: W. M. Kazmierski, C. J. Aquino, N. Bifulco, E. E. Boros, B. A. Chauder, P. Y. Chong, M. Duan, F. Deanda, C. S. Koble, E. W. Mclean, J. P. Peckham, A. C. Perkins, J. B. Thompson, D. Vanderwall. WO Patent 2004 054 974 A2, 2004.
32. a) S. D. Larsen, P. A. Grieco, J. Am. Chem. Soc. 1985, 107, 1768-1769;
33. b) K. Waldmann, Liebigs Ann. Chem. 1989, 231:
34. c) S. Körbe. A. de Meijere, T. Labahn, Helv. Chim. Acta 2002, 85, 3161-3175.
35. S. E. Gibson, N. Guillo, M. J. Tozer, Tetrahedron 1999. 55, 585-615.
36. D. Laurie, E. Lucas, D. C. Nonhebel, C. J. Suckling, Tetrahedron 1986, 42, 1035-1046.
37. L. Wessjohann, N. Krass, D. Yu, A. de Meijere, Chem. Ber. 1992, 125, 867-882.
38. K. O. Hallinan, D. H. G. Crout, W. Errington, J. Chem. Soc., Perkin Trans, 1 1994, 3537-3543.
39. a) A. L. Castelliano, S. Horne, G. J. Taylor. R. Billedeau, A. Krantz, Tetrahedron 1988, 44, 5451-5466;
40. b) A. L. Castelliano, S. Horne, R. Billedeau, A. Krantz, Tetrahedron Lett. 1986, 27, 2435-2438.