A short, efficient, and stereoselective procedure for the synthesis of cis-3-hydroxymethyl-aziridine-2-carboxylic acid derivatives, important intermediates in the synthesis of mitomycinoids

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6780-6783

  Fernández Megía, Eduardo ^a   Montaos, Marco A ^a   Sardina, F Javier ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYMETHYL AZIRIDINE 2 CARBOXYLIC ACID DERIVATIVE; 4 FORMYL 6,9 DIHYDROXY 14 OXA 1,11 DIAZATETRACYCLO[7.4.1.0 2,7 0 10,12]TETRADECA 2,4,6 TRIEN 8 YLMETHYLCARBAMATE; ASPARTIC ACID; METHYL 3 METHANOSULFONYLOXYMETHYL 1 (9' PHENYLFLUOREN 9' YL)AZIRIDINE CARBOXYLATE; METHYL 3 TOLUENSULFONYLOXYMETHYL 1 (9' PHENYLFLUOREN 9' YL)AZIRIDINE CARBOXYLATE; MITOMYCIN C; MITOMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; DRUG CONFORMATION; DRUG SYNTHESIS; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM;

ANTIBIOTICS, ANTINEOPLASTIC; AZIRIDINES; INDICATORS AND REAGENTS; MITOMYCINS;

EID: 0343443090     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000732+     Document Type: Article

References (47)

1. Danishefsky, S. J.; Schkeryantz, J. M. Synlett 1995, 475.
2. Williams, R. M.; Rollins, S. B.; Judd, T. C. Tetrahedron 2000, 56, 521.
3. Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723.
4. Total syntheses: (a) Fukuyama, T.; Nakatsubo, F.; Cocuzza, A. J.; Kishi, Y. Tetrahedron Lett. 1977, 18, 4295. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303. (d) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (e) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (f) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (g) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (h) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
5. Total syntheses: (a) Fukuyama, T.; Nakatsubo, F.; Cocuzza, A. J.; Kishi, Y. Tetrahedron Lett. 1977, 18, 4295. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303. (d) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (e) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (f) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (g) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (h) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
6. Total syntheses: (a) Fukuyama, T.; Nakatsubo, F.; Cocuzza, A. J.; Kishi, Y. Tetrahedron Lett. 1977, 18, 4295. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303. (d) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (e) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (f) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (g) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (h) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
7. Total syntheses: (a) Fukuyama, T.; Nakatsubo, F.; Cocuzza, A. J.; Kishi, Y. Tetrahedron Lett. 1977, 18, 4295. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303. (d) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (e) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (f) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (g) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (h) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
8. Total syntheses: (a) Fukuyama, T.; Nakatsubo, F.; Cocuzza, A. J.; Kishi, Y. Tetrahedron Lett. 1977, 18, 4295. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303. (d) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (e) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (f) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (g) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (h) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
9. Total syntheses: (a) Fukuyama, T.; Nakatsubo, F.; Cocuzza, A. J.; Kishi, Y. Tetrahedron Lett. 1977, 18, 4295. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303. (d) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (e) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (f) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (g) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (h) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
10. Total syntheses: (a) Fukuyama, T.; Nakatsubo, F.; Cocuzza, A. J.; Kishi, Y. Tetrahedron Lett. 1977, 18, 4295. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303. (d) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (e) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (f) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (g) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (h) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
11. Total syntheses: (a) Fukuyama, T.; Nakatsubo, F.; Cocuzza, A. J.; Kishi, Y. Tetrahedron Lett. 1977, 18, 4295. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303. (d) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (e) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (f) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (g) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (h) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
12. Jones, R. J.; Rapoport, H. J. Org. Chem. 1990, 55, 1144.
13. The nucleophilic displacement of an activated derivative of the hydroxyl group in 1a in the context of mitomycinoids' synthesis has been reported by Rapoport (ref 5).
14. (a) Fujisawa, T.; Hayakawa, R.; Shimizu, M. Tetrahedron Lett. 1992, 33, 7903.
15. (b) For a racemic synthesis of 1c (R = MOM, PG = Tr, X = OEt) involving a lithiated aziridine see: Vedejs, E.; Moss, W. O. J. Am. Chem. Soc. 1993, 115, 1607.
16. (c) For the synthesis of a trans analogue of 1 see: Ziegler, F. E.; Belema, M. J. Org. Chem. 1994, 59, 7962.
17. (d) Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243 and references therein.
18. (e) Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651.
19. (f) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631.
20. (g) Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488.
21. (h) McLaren, A. B.; Sweeney, J. B. Org. Lett. 1999, 1, 1339.
22. (i) For a synthesis of N-alkoxy analogues of 1 see: Hanessian, S.; Cantin, L.-D. Tetrahedron Lett. 2000, 41, 787.
23. Reviews on aziridine synthesis: (a) Tanner, D. Pure Appl. Chem. 1993, 65, 1319. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (c) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1A, p 1. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
24. Reviews on aziridine synthesis: (a) Tanner, D. Pure Appl. Chem. 1993, 65, 1319. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (c) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1A, p 1. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
25. Reviews on aziridine synthesis: (a) Tanner, D. Pure Appl. Chem. 1993, 65, 1319. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (c) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1A, p 1. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
26. Reviews on aziridine synthesis: (a) Tanner, D. Pure Appl. Chem. 1993, 65, 1319. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (c) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1A, p 1. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
27. Reviews on aziridine synthesis: (a) Tanner, D. Pure Appl. Chem. 1993, 65, 1319. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (c) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1A, p 1. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
28. Poch, M.; Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 6935.
29. Diester 2 was synthesised by diastereoselective hydroxylation of N-Pf-aspartate enolates (60%, three steps from L-aspartic acid) as described in (a) Fernández-Megía, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. For alternative methods for the synthesis of hydroxyaspartates see: (c) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401 and references therein. (d) Charvillon, F. B.; Amouroux, R. Synth. Commun. 1997, 27, 395 and references therein. (e) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Synlett 1999, 1727.
30. Diester 2 was synthesised by diastereoselective hydroxylation of N-Pf-aspartate enolates (60%, three steps from L-aspartic acid) as described in (a) Fernández-Megía, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. For alternative methods for the synthesis of hydroxyaspartates see: (c) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401 and references therein. (d) Charvillon, F. B.; Amouroux, R. Synth. Commun. 1997, 27, 395 and references therein. (e) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Synlett 1999, 1727.
31. Diester 2 was synthesised by diastereoselective hydroxylation of N-Pf-aspartate enolates (60%, three steps from L-aspartic acid) as described in (a) Fernández-Megía, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. For alternative methods for the synthesis of hydroxyaspartates see: (c) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401 and references therein. (d) Charvillon, F. B.; Amouroux, R. Synth. Commun. 1997, 27, 395 and references therein. (e) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Synlett 1999, 1727.
32. Diester 2 was synthesised by diastereoselective hydroxylation of N-Pf-aspartate enolates (60%, three steps from L-aspartic acid) as described in (a) Fernández-Megía, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. For alternative methods for the synthesis of hydroxyaspartates see: (c) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401 and references therein. (d) Charvillon, F. B.; Amouroux, R. Synth. Commun. 1997, 27, 395 and references therein. (e) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Synlett 1999, 1727.
33. Diester 2 was synthesised by diastereoselective hydroxylation of N-Pf-aspartate enolates (60%, three steps from L-aspartic acid) as described in (a) Fernández-Megía, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. For alternative methods for the synthesis of hydroxyaspartates see: (c) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401 and references therein. (d) Charvillon, F. B.; Amouroux, R. Synth. Commun. 1997, 27, 395 and references therein. (e) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Synlett 1999, 1727.
34. Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389.
35. Tsuboi, S.; Furutani, H.; Utaka, M.; Takeda, A. Tetrahedron Lett. 1987, 28, 2709.
36. Lower yields of 3 (77%) along with some of the corresponding triol from overreduction (5%) were obtained.
37. 13C NMR spectroacopic data and by comparison with compound 1a (ref 5). See also ref 8c.
38. 13C NMR spectroscopic data and by comparison with reported data in the literature: (a) Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201. (b) Blythin, D. J.; Green, M. J.; Lauzon, M. J. R.; Shue, H.-J. J. Org. Chem. 1994, 59, 6098. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1B, p 507. For syntheses of azetidine-2-carboxylic acid derivatives see also: (d) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 265. (e) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717. (f) Hanessian, S.; Bernstein, N.; Yang, R.-Y.; Maguire, R. Bioorg. Med. Chem. Lett. 1999, 9, 1437 and references therein.
39. 13C NMR spectroscopic data and by comparison with reported data in the literature: (a) Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201. (b) Blythin, D. J.; Green, M. J.; Lauzon, M. J. R.; Shue, H.-J. J. Org. Chem. 1994, 59, 6098. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1B, p 507. For syntheses of azetidine-2-carboxylic acid derivatives see also: (d) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 265. (e) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717. (f) Hanessian, S.; Bernstein, N.; Yang, R.-Y.; Maguire, R. Bioorg. Med. Chem. Lett. 1999, 9, 1437 and references therein.
40. 13C NMR spectroscopic data and by comparison with reported data in the literature: (a) Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201. (b) Blythin, D. J.; Green, M. J.; Lauzon, M. J. R.; Shue, H.-J. J. Org. Chem. 1994, 59, 6098. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1B, p 507. For syntheses of azetidine-2-carboxylic acid derivatives see also: (d) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 265. (e) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717. (f) Hanessian, S.; Bernstein, N.; Yang, R.-Y.; Maguire, R. Bioorg. Med. Chem. Lett. 1999, 9, 1437 and references therein.
41. 13C NMR spectroscopic data and by comparison with reported data in the literature: (a) Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201. (b) Blythin, D. J.; Green, M. J.; Lauzon, M. J. R.; Shue, H.-J. J. Org. Chem. 1994, 59, 6098. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1B, p 507. For syntheses of azetidine-2-carboxylic acid derivatives see also: (d) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 265. (e) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717. (f) Hanessian, S.; Bernstein, N.; Yang, R.-Y.; Maguire, R. Bioorg. Med. Chem. Lett. 1999, 9, 1437 and references therein.
42. 13C NMR spectroscopic data and by comparison with reported data in the literature: (a) Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201. (b) Blythin, D. J.; Green, M. J.; Lauzon, M. J. R.; Shue, H.-J. J. Org. Chem. 1994, 59, 6098. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1B, p 507. For syntheses of azetidine-2-carboxylic acid derivatives see also: (d) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 265. (e) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717. (f) Hanessian, S.; Bernstein, N.; Yang, R.-Y.; Maguire, R. Bioorg. Med. Chem. Lett. 1999, 9, 1437 and references therein.
43. 13C NMR spectroscopic data and by comparison with reported data in the literature: (a) Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201. (b) Blythin, D. J.; Green, M. J.; Lauzon, M. J. R.; Shue, H.-J. J. Org. Chem. 1994, 59, 6098. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 1B, p 507. For syntheses of azetidine-2-carboxylic acid derivatives see also: (d) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 265. (e) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717. (f) Hanessian, S.; Bernstein, N.; Yang, R.-Y.; Maguire, R. Bioorg. Med. Chem. Lett. 1999, 9, 1437 and references therein.
44. 4 or DIBALH led to the formation of substantial amounts of the corresponding γ-butyrolactone.
45. Ambrosi, H.-D.; Duczek, W.; Ramm, M.; Jähnisch, K. Tetrahedron Lett. 1994, 35, 7613.
46. For the successful deprotection of a N-trityl aziridine-2-carboxylate see: Korn, A.; Rudolph-Böhner, S.; Moroder, L. Tetrahedron 1994, 50, 1717.
47. Blanco, M.-J.; Sardina, F. J. J. Org. Chem. 1996, 61, 4748.