Asymmetric synthesis with 6-tert-butyl-5-methoxy-6-methyl-3,6-dihydro-2H-1,4-oxazin-2-one as a new chiral glycine equivalent: Preparation of enantiomerically pure α-tertiary and α-quaternary α-amino acids

European Journal of Organic Chemistry

Volumn , Issue 7, 2003, Pages 1244-1263

  Koch, Claus Jürgen ^a   Šimonyiová, Soňa ^a   Pabel, Jörg ^a   Kärtner, Annerose ^a   Polborn, Kurt ^a   Wanner, Klaus Theodor ^a  

^a LUDWIG MAXIMILIANS UNIVERSITY   (Germany)

Author keywords

Amino acids; Asymmetric synthesis; Carboxylic acids; Glycine equivalent; Hydroxy acids

Indexed keywords

(3 BENZYL 6 TERT BUTYL 5 METHOXY 6 METHYL 2 OXO 3,6 DIHYDRO 2H 1,4 OXAZIN 3 YL)PERACETATE; 1 (6 TERT BUTYL 5 METHOXY 6 METHYL 8 OXO 7 OXA 4 AZASPIRO[2.5]OCT 4 EN 1 YLMETHYL) 3 PHENYL 1 (TRIFLUOROACETYL)UREA; 1 (6 TERT BUTYL 5 METHOXY 6 METHYL 8 OXO 7 OXA 4 AZASPIRO[2.5]OCT 4 EN 1YLMETHYL) 3 PHENYLUREA; 1 PHENYL 3 (TRIFLUOROACETYL)UREA; 3 BENZYL 3 N BUTYL 6 TERT BUTYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 3 BENZYL 6 TERT BUTYL 3 HYDROPEROXY 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 3 BENZYL 6 TERT BUTYL 3 ISOPROPYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 3 BENZYL 6 TERT BUTYL 5 METHOXY 3,6 DIMETHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 3 BENZYL 6 TERT BUTYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 3 N BUTYL 6 TERT BUTYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 3,3 DI N BUTYL 6 TERT BUTYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 3,3 DIBENZYL 6 TERT BUTYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 6 TERT BUTYL 1 HYDROXYMETHYL 5 METHOXY 6 METHYL 7 OXA 4 AZASPIRO[2.5]OCT 4 EN 8 ONE; 6 TERT BUTYL 3 (2 HYDROXYETHYLIDENE) 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 6 TERT BUTYL 3 ISOPROPYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 6 TERT BUTYL 3,3 DIISOPROPYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 6 TERT BUTYL 5 METHOXY 3,6 DIMETHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 6 TERT BUTYL 5 METHOXY 6 METHYL 1 PHENYLAMINOMETHYL 7 OXA 4 AZASPIRO[2.5]OCT 4 EN 8 ONE; 6 TERT BUTYL 5 METHOXY 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; 6 TERT BUTYL 5 METHOXY 6 METHYL 8 OXO 7 OXA 4 AZASPIRO[2.5]OCT 4 ENE 1 CARBALDEHYDE; 6 TERT BUTYL 5 METHOXY METHYL 6 METHYL 3,6 DIHYDRO 2H 1,4 OXAZIN 2 ONE; ALDEHYDE DERIVATIVE; ALPHA HYDROXYCARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; OXAZINE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ALKYLATION; AMINATION; ARTICLE; ENANTIOMER; HYDROLYSIS; OPTICAL RESOLUTION; OXIDATION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037391660     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390179     Document Type: Article

References (73)

1. [1a] T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
2. [1a] T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
3. [1b] B. M. Trost, X. Ariza, Angew. Chem. 1997, 109, 2749-2751; Angew. Chem. Int. Ed. Engl. 1997, 36, 2635-2637.
4. [1b] B. M. Trost, X. Ariza, Angew. Chem. 1997, 109, 2749-2751; Angew. Chem. Int. Ed. Engl. 1997, 36, 2635-2637.
5. [1c] S. Hanessian, G. McNaughton-Smith, H. G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854.
6. [2a] M. Goodman, H. Shao, Pure Appl. Chem. 1996, 68, 1303-1308 and references therein.
7. [2b] W. F. Degrado, Adv. Protein Chem. 1988, 39, 51-124 and references therein.
8. [3a] C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 1998, 9, 3517-3599.
9. [3b] C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 2000, 11, 645-732.
10. O. Achatz, A. Grandl, K. Th. Wanner, Eur. J. Org. Chem. 1999, 1967-1978.
11. Camphanic acid, which is commercially available in both enantiomeric forms, serves as a starting material for the synthesis of the chiral auxiliary. For large-scale synthesis it is more economic to prepare it from the corresponding enantiomer of camphoric acid. However, the (-)-enantiomer of camphoric acid is far more expensive than the (+)-enantiomer.
12. [6a] R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989.
13. [6b] R. Fitzi, D. Seebach, Tetrahedron 1988, 44, 5277-5292.
14. [7a] G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Assymetry 1998, 9, 119-132. [7b] G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1998, 9, 3411-3420. [7c] R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286. [7d] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 5925-5936. [7e] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 2309-2322. [7f] T. Abellán, C. Nájera, J. M. Sansano, Tetrahedron: Asymmetry 1998, 9, 2211-2214. For a review on asymmetric synthesis of aquaternary aminocyclopropanecarboxyclic acids see: K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583. A related chiral glycine equivalent based on atrolactic acid has recently been reported: S. N. Crane, E. J. Corey, Organic Letters 2001, 3, 1395-1397.
15. [7a] G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Assymetry 1998, 9, 119-132. [7b] G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1998, 9, 3411-3420. [7c] R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286. [7d] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 5925-5936. [7e] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 2309-2322. [7f] T. Abellán, C. Nájera, J. M. Sansano, Tetrahedron: Asymmetry 1998, 9, 2211-2214. For a review on asymmetric synthesis of aquaternary aminocyclopropanecarboxyclic acids see: K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583. A related chiral glycine equivalent based on atrolactic acid has recently been reported: S. N. Crane, E. J. Corey, Organic Letters 2001, 3, 1395-1397.
16. [7a] G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Assymetry 1998, 9, 119-132. [7b] G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1998, 9, 3411-3420. [7c] R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286. [7d] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 5925-5936. [7e] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 2309-2322. [7f] T. Abellán, C. Nájera, J. M. Sansano, Tetrahedron: Asymmetry 1998, 9, 2211-2214. For a review on asymmetric synthesis of aquaternary aminocyclopropanecarboxyclic acids see: K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583. A related chiral glycine equivalent based on atrolactic acid has recently been reported: S. N. Crane, E. J. Corey, Organic Letters 2001, 3, 1395-1397.
17. [7a] G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Assymetry 1998, 9, 119-132. [7b] G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1998, 9, 3411-3420. [7c] R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286. [7d] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 5925-5936. [7e] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 2309-2322. [7f] T. Abellán, C. Nájera, J. M. Sansano, Tetrahedron: Asymmetry 1998, 9, 2211-2214. For a review on asymmetric synthesis of aquaternary aminocyclopropanecarboxyclic acids see: K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583. A related chiral glycine equivalent based on atrolactic acid has recently been reported: S. N. Crane, E. J. Corey, Organic Letters 2001, 3, 1395-1397.
18. [7a] G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Assymetry 1998, 9, 119-132. [7b] G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1998, 9, 3411-3420. [7c] R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286. [7d] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 5925-5936. [7e] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 2309-2322. [7f] T. Abellán, C. Nájera, J. M. Sansano, Tetrahedron: Asymmetry 1998, 9, 2211-2214. For a review on asymmetric synthesis of aquaternary aminocyclopropanecarboxyclic acids see: K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583. A related chiral glycine equivalent based on atrolactic acid has recently been reported: S. N. Crane, E. J. Corey, Organic Letters 2001, 3, 1395-1397.
19. [7a] G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Assymetry 1998, 9, 119-132. [7b] G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1998, 9, 3411-3420. [7c] R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286. [7d] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 5925-5936. [7e] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 2309-2322. [7f] T. Abellán, C. Nájera, J. M. Sansano, Tetrahedron: Asymmetry 1998, 9, 2211-2214. For a review on asymmetric synthesis of aquaternary aminocyclopropanecarboxyclic acids see: K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583. A related chiral glycine equivalent based on atrolactic acid has recently been reported: S. N. Crane, E. J. Corey, Organic Letters 2001, 3, 1395-1397.
20. [7a] G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Assymetry 1998, 9, 119-132. [7b] G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1998, 9, 3411-3420. [7c] R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286. [7d] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 5925-5936. [7e] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 2309-2322. [7f] T. Abellán, C. Nájera, J. M. Sansano, Tetrahedron: Asymmetry 1998, 9, 2211-2214. For a review on asymmetric synthesis of aquaternary aminocyclopropanecarboxyclic acids see: K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583. A related chiral glycine equivalent based on atrolactic acid has recently been reported: S. N. Crane, E. J. Corey, Organic Letters 2001, 3, 1395-1397.
21. [7a] G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Assymetry 1998, 9, 119-132. [7b] G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1998, 9, 3411-3420. [7c] R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286. [7d] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 5925-5936. [7e] K. Hammer, K. Undheim, Tetrahedron 1997, 53, 2309-2322. [7f] T. Abellán, C. Nájera, J. M. Sansano, Tetrahedron: Asymmetry 1998, 9, 2211-2214. For a review on asymmetric synthesis of aquaternary aminocyclopropanecarboxyclic acids see: K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583. A related chiral glycine equivalent based on atrolactic acid has recently been reported: S. N. Crane, E. J. Corey, Organic Letters 2001, 3, 1395-1397.
22. For further investigations on lithio-aggregates formed in ethereal solvents see: [8a] D. Z. Wang, Y.-J. Kim, A. Streitwieser, J. Am. Chem. Soc. 2000, 122, 10754-10760. [8b] J. H. Horner, M. Vera, J. B. Grutzner, J. Org. Chem. 1986, 51, 4212-4220. [8c] L. M. Jackman, B. C. Lange, Tetrahedron 1977, 33, 2737-2769. [8d] E. M. Arnett, C. A. Palmer, J. Am. Chem. Soc. 1990, 112, 7354-7360. [8e] A. Streitwieser, S. S.-W. Leung, Y.-J. Kim, Org. Lett. 1999, 1, 145-147. [8f] A. Streitwieser, D. Z.-R. Wang, J. Am. Chem. Soc. 1999, 121, 6213-6219. [8g] D. Z.-R. Wang, A. Streitwieser, Can. J. Chem. 1999, 77, 654-658.
23. For further investigations on lithio-aggregates formed in ethereal solvents see: [8a] D. Z. Wang, Y.-J. Kim, A. Streitwieser, J. Am. Chem. Soc. 2000, 122, 10754-10760. [8b] J. H. Horner, M. Vera, J. B. Grutzner, J. Org. Chem. 1986, 51, 4212-4220. [8c] L. M. Jackman, B. C. Lange, Tetrahedron 1977, 33, 2737-2769. [8d] E. M. Arnett, C. A. Palmer, J. Am. Chem. Soc. 1990, 112, 7354-7360. [8e] A. Streitwieser, S. S.-W. Leung, Y.-J. Kim, Org. Lett. 1999, 1, 145-147. [8f] A. Streitwieser, D. Z.-R. Wang, J. Am. Chem. Soc. 1999, 121, 6213-6219. [8g] D. Z.-R. Wang, A. Streitwieser, Can. J. Chem. 1999, 77, 654-658.
24. For further investigations on lithio-aggregates formed in ethereal solvents see: [8a] D. Z. Wang, Y.-J. Kim, A. Streitwieser, J. Am. Chem. Soc. 2000, 122, 10754-10760. [8b] J. H. Horner, M. Vera, J. B. Grutzner, J. Org. Chem. 1986, 51, 4212-4220. [8c] L. M. Jackman, B. C. Lange, Tetrahedron 1977, 33, 2737-2769. [8d] E. M. Arnett, C. A. Palmer, J. Am. Chem. Soc. 1990, 112, 7354-7360. [8e] A. Streitwieser, S. S.-W. Leung, Y.-J. Kim, Org. Lett. 1999, 1, 145-147. [8f] A. Streitwieser, D. Z.-R. Wang, J. Am. Chem. Soc. 1999, 121, 6213-6219. [8g] D. Z.-R. Wang, A. Streitwieser, Can. J. Chem. 1999, 77, 654-658.
25. For further investigations on lithio-aggregates formed in ethereal solvents see: [8a] D. Z. Wang, Y.-J. Kim, A. Streitwieser, J. Am. Chem. Soc. 2000, 122, 10754-10760. [8b] J. H. Horner, M. Vera, J. B. Grutzner, J. Org. Chem. 1986, 51, 4212-4220. [8c] L. M. Jackman, B. C. Lange, Tetrahedron 1977, 33, 2737-2769. [8d] E. M. Arnett, C. A. Palmer, J. Am. Chem. Soc. 1990, 112, 7354-7360. [8e] A. Streitwieser, S. S.-W. Leung, Y.-J. Kim, Org. Lett. 1999, 1, 145-147. [8f] A. Streitwieser, D. Z.-R. Wang, J. Am. Chem. Soc. 1999, 121, 6213-6219. [8g] D. Z.-R. Wang, A. Streitwieser, Can. J. Chem. 1999, 77, 654-658.
26. For further investigations on lithio-aggregates formed in ethereal solvents see: [8a] D. Z. Wang, Y.-J. Kim, A. Streitwieser, J. Am. Chem. Soc. 2000, 122, 10754-10760. [8b] J. H. Horner, M. Vera, J. B. Grutzner, J. Org. Chem. 1986, 51, 4212-4220. [8c] L. M. Jackman, B. C. Lange, Tetrahedron 1977, 33, 2737-2769. [8d] E. M. Arnett, C. A. Palmer, J. Am. Chem. Soc. 1990, 112, 7354-7360. [8e] A. Streitwieser, S. S.-W. Leung, Y.-J. Kim, Org. Lett. 1999, 1, 145-147. [8f] A. Streitwieser, D. Z.-R. Wang, J. Am. Chem. Soc. 1999, 121, 6213-6219. [8g] D. Z.-R. Wang, A. Streitwieser, Can. J. Chem. 1999, 77, 654-658.
27. For further investigations on lithio-aggregates formed in ethereal solvents see: [8a] D. Z. Wang, Y.-J. Kim, A. Streitwieser, J. Am. Chem. Soc. 2000, 122, 10754-10760. [8b] J. H. Horner, M. Vera, J. B. Grutzner, J. Org. Chem. 1986, 51, 4212-4220. [8c] L. M. Jackman, B. C. Lange, Tetrahedron 1977, 33, 2737-2769. [8d] E. M. Arnett, C. A. Palmer, J. Am. Chem. Soc. 1990, 112, 7354-7360. [8e] A. Streitwieser, S. S.-W. Leung, Y.-J. Kim, Org. Lett. 1999, 1, 145-147. [8f] A. Streitwieser, D. Z.-R. Wang, J. Am. Chem. Soc. 1999, 121, 6213-6219. [8g] D. Z.-R. Wang, A. Streitwieser, Can. J. Chem. 1999, 77, 654-658.
28. For further investigations on lithio-aggregates formed in ethereal solvents see: [8a] D. Z. Wang, Y.-J. Kim, A. Streitwieser, J. Am. Chem. Soc. 2000, 122, 10754-10760. [8b] J. H. Horner, M. Vera, J. B. Grutzner, J. Org. Chem. 1986, 51, 4212-4220. [8c] L. M. Jackman, B. C. Lange, Tetrahedron 1977, 33, 2737-2769. [8d] E. M. Arnett, C. A. Palmer, J. Am. Chem. Soc. 1990, 112, 7354-7360. [8e] A. Streitwieser, S. S.-W. Leung, Y.-J. Kim, Org. Lett. 1999, 1, 145-147. [8f] A. Streitwieser, D. Z.-R. Wang, J. Am. Chem. Soc. 1999, 121, 6213-6219. [8g] D. Z.-R. Wang, A. Streitwieser, Can. J. Chem. 1999, 77, 654-658.
29. [9a] I. A. Faworskaja, J. Gen. Chem. (U. S. S. R.) 1948, 18, 52-59; Chem. Abstr. 1948, 42, 4905d. [9b] A. Richard, Ann. Chim. (Paris) 1910, 21, 360-406. [9c] M. B. Green, W. J. Hickinbottom, J. Org. Chem. 1957, 22, 3262-3270. For an already existing asymmetric synthesis of 1 see: [9d] E. L. Eliel, J. E. Lynch, W. R. Kenan Jr., Tetrahedron Lett. 1987, 28, 4813-4816. [9e] R. J. D. Evans, S. R. Landor, J. Chem. Soc. 1965, 2553-2559. [9f] S. Ahmad, S. H. Spergel, J. C. Barrish, J. DiMarco, J. Gougoutas, Tetrahedron: Asymmetry 1995, 6, 2893-2894.
30. [9a] I. A. Faworskaja, J. Gen. Chem. (U. S. S. R.) 1948, 18, 52-59; Chem. Abstr. 1948, 42, 4905d. [9b] A. Richard, Ann. Chim. (Paris) 1910, 21, 360-406. [9c] M. B. Green, W. J. Hickinbottom, J. Org. Chem. 1957, 22, 3262-3270. For an already existing asymmetric synthesis of 1 see: [9d] E. L. Eliel, J. E. Lynch, W. R. Kenan Jr., Tetrahedron Lett. 1987, 28, 4813-4816. [9e] R. J. D. Evans, S. R. Landor, J. Chem. Soc. 1965, 2553-2559. [9f] S. Ahmad, S. H. Spergel, J. C. Barrish, J. DiMarco, J. Gougoutas, Tetrahedron: Asymmetry 1995, 6, 2893-2894.
31. [9a] I. A. Faworskaja, J. Gen. Chem. (U. S. S. R.) 1948, 18, 52-59; Chem. Abstr. 1948, 42, 4905d. [9b] A. Richard, Ann. Chim. (Paris) 1910, 21, 360-406. [9c] M. B. Green, W. J. Hickinbottom, J. Org. Chem. 1957, 22, 3262-3270. For an already existing asymmetric synthesis of 1 see: [9d] E. L. Eliel, J. E. Lynch, W. R. Kenan Jr., Tetrahedron Lett. 1987, 28, 4813-4816. [9e] R. J. D. Evans, S. R. Landor, J. Chem. Soc. 1965, 2553-2559. [9f] S. Ahmad, S. H. Spergel, J. C. Barrish, J. DiMarco, J. Gougoutas, Tetrahedron: Asymmetry 1995, 6, 2893-2894.
32. [9a] I. A. Faworskaja, J. Gen. Chem. (U. S. S. R.) 1948, 18, 52-59; Chem. Abstr. 1948, 42, 4905d. [9b] A. Richard, Ann. Chim. (Paris) 1910, 21, 360-406. [9c] M. B. Green, W. J. Hickinbottom, J. Org. Chem. 1957, 22, 3262-3270. For an already existing asymmetric synthesis of 1 see: [9d] E. L. Eliel, J. E. Lynch, W. R. Kenan Jr., Tetrahedron Lett. 1987, 28, 4813-4816. [9e] R. J. D. Evans, S. R. Landor, J. Chem. Soc. 1965, 2553-2559. [9f] S. Ahmad, S. H. Spergel, J. C. Barrish, J. DiMarco, J. Gougoutas, Tetrahedron: Asymmetry 1995, 6, 2893-2894.
33. [9a] I. A. Faworskaja, J. Gen. Chem. (U. S. S. R.) 1948, 18, 52-59; Chem. Abstr. 1948, 42, 4905d. [9b] A. Richard, Ann. Chim. (Paris) 1910, 21, 360-406. [9c] M. B. Green, W. J. Hickinbottom, J. Org. Chem. 1957, 22, 3262-3270. For an already existing asymmetric synthesis of 1 see: [9d] E. L. Eliel, J. E. Lynch, W. R. Kenan Jr., Tetrahedron Lett. 1987, 28, 4813-4816. [9e] R. J. D. Evans, S. R. Landor, J. Chem. Soc. 1965, 2553-2559. [9f] S. Ahmad, S. H. Spergel, J. C. Barrish, J. DiMarco, J. Gougoutas, Tetrahedron: Asymmetry 1995, 6, 2893-2894.
34. [9a] I. A. Faworskaja, J. Gen. Chem. (U. S. S. R.) 1948, 18, 52-59; Chem. Abstr. 1948, 42, 4905d. [9b] A. Richard, Ann. Chim. (Paris) 1910, 21, 360-406. [9c] M. B. Green, W. J. Hickinbottom, J. Org. Chem. 1957, 22, 3262-3270. For an already existing asymmetric synthesis of 1 see: [9d] E. L. Eliel, J. E. Lynch, W. R. Kenan Jr., Tetrahedron Lett. 1987, 28, 4813-4816. [9e] R. J. D. Evans, S. R. Landor, J. Chem. Soc. 1965, 2553-2559. [9f] S. Ahmad, S. H. Spergel, J. C. Barrish, J. DiMarco, J. Gougoutas, Tetrahedron: Asymmetry 1995, 6, 2893-2894.
35. [9a] I. A. Faworskaja, J. Gen. Chem. (U. S. S. R.) 1948, 18, 52-59; Chem. Abstr. 1948, 42, 4905d. [9b] A. Richard, Ann. Chim. (Paris) 1910, 21, 360-406. [9c] M. B. Green, W. J. Hickinbottom, J. Org. Chem. 1957, 22, 3262-3270. For an already existing asymmetric synthesis of 1 see: [9d] E. L. Eliel, J. E. Lynch, W. R. Kenan Jr., Tetrahedron Lett. 1987, 28, 4813-4816. [9e] R. J. D. Evans, S. R. Landor, J. Chem. Soc. 1965, 2553-2559. [9f] S. Ahmad, S. H. Spergel, J. C. Barrish, J. DiMarco, J. Gougoutas, Tetrahedron: Asymmetry 1995, 6, 2893-2894.
36. 4 see: A. Abiko, S. Masamune, Tetrahedron Lett. 1992, 33, 5517-5518.
37. H. Brückner, Chromatographia 1987, 24, 725-738.
38. E. Bald, K. Saigo, T. Mukaiyama, Chem. Lett. 1975, 1163-1167.
39. U. Schöllkopf, U. Groth, C. Deng, Angew. Chem. 1981, 93, 793-795; Angew. Chem. Int. Ed. Engl. 1981, 20, 798-799.
40. U. Schöllkopf, U. Groth, C. Deng, Angew. Chem. 1981, 93, 793-795; Angew. Chem. Int. Ed. Engl. 1981, 20, 798-799.
41. [14a] J. E. Baldwin, V. Lee, C. J. Schofield, Heterocycles 1992, 34, 903-906.
42. [14b] D. Seebach, J. D. Aebi, R. Naef, T. Weber, Helv. Chim. Acta 1985, 68, 144-154.
43. Crystallographic data for structure 21 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 192162. Copies of the data can be obtained free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: (internat.) +44 1223 336033 or E-mail: deposit@ccdc.cam.ac.uk. The X-ray diffraction analysis of 22 was performed by M. Malecka and E. Budzisz at the University of Lodz and will be published by these authors.
44. M. C. Pirrung, S. E. Dunlap, U. P. Trinks, Helv. Chim. Acta 1989, 72, 1301-1310.
45. [4] is in disagreement with the results described in the present paper and will have to be reevaluated, as the assignment then was based only on the optical rotation of the final amino acids.
46. [18a] J. Furukawa, N. Kawabata, J. Nishimura, Tetrahedron 1968, 24, 53-59.
47. [18b] J. Furukawa, N. Kawabata, Adv. Organomet. Chem. 1974, 12, 83-134.
48. [19a] O. Mitsunobu, M. Yamada, Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382.
49. [19b] O. Mitsunobu, Synthesis 1981, 1-28.
50. [19c] O. Mitsunobu, M. Wada, T. Sano, J. Am. Chem. Soc. 1972, 94, 679-680.
51. [19d] O. Mitsunobu, M. Yamada, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1967, 40, 935-939.
52. [19e] T. Tsunoda, Y Yamamiya, S. Ito, Tetrahedron Lett. 1993, 34, 1639-1642.
53. B. A. Arbuzov, N. N. Zobova, N. R. Rubinova, Ser. Khim. 1976, 1, 202-204.
54. For a synthesis of the free racemic 1-amino-2-{(3-phenylureido)methyl}cyclopropanecarboxylic acid see: C. Balsamini, A. Bedini, G. Spadoni, G. Tarzia, A. Tontini, Farmaco 1998, 53, 181-188.
55. TFA proved to be better than HCl, as the lactam also was formed to some extent with the latter. This phenomenon is well known and has been explained in terms of the higher nucleophilicity of the chloride ion than of the trifluoroacetate ion, see: T. Beulshausen, U. Groth, U. Schöllkopf, Liebigs Ann. Chem. 1991, 1207-1209.
56. For examples of hydrolysis of similar substrates under similar conditions see: G. Kardassis, P. Brungs, C. Nothhelfer, E. Steckhan, Tetrahedron 1998, 54, 3479-3488.
57. 3SiI, which is known to cause this type of reaction; see: [24a] R. D. Miller, D. R. McKean, Tetrahedron Lett. 1979, 20, 2305-2308. [24b] E. W. Logusch, Tetrahedron Lett. 1984, 25, 4195-4198. [24c] M. Ihara, T. Taniguchi, Y. Tokunaga, K. Fukumoto, J. Org. Chem. 1994, 59, 8092-8100.
58. 3SiI, which is known to cause this type of reaction; see: [24a] R. D. Miller, D. R. McKean, Tetrahedron Lett. 1979, 20, 2305-2308. [24b] E. W. Logusch, Tetrahedron Lett. 1984, 25, 4195-4198. [24c] M. Ihara, T. Taniguchi, Y. Tokunaga, K. Fukumoto, J. Org. Chem. 1994, 59, 8092-8100.
59. 3SiI, which is known to cause this type of reaction; see: [24a] R. D. Miller, D. R. McKean, Tetrahedron Lett. 1979, 20, 2305-2308. [24b] E. W. Logusch, Tetrahedron Lett. 1984, 25, 4195-4198. [24c] M. Ihara, T. Taniguchi, Y. Tokunaga, K. Fukumoto, J. Org. Chem. 1994, 59, 8092-8100.
60. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
61. C. Glücksmann, Monatsh. Chem. 1889, 10, 770-782.
62. M. R. Heilmann, Bull. Soc. Chim. Fr. 1929, 45, 412-414.
63. E. Fischer, A. Mouneyrat, Ber. Dtsch. Chem. Ges. 1900, 33, 2384-2385.
64. G. Porzi, S. Sandri, Tetrahedron: Asymmetry 1996, 7, 189-196.
65. Q. B. Broxterman, B. Kaptein, J. Kamphuis, H. E. Shoemaker, J. Org. Chem. 1992, 57, 6286-6294.
66. J. Mulzer, A. Angermann, B. Schubert, C. Seilz, J. Org. Chem. 1986, 51, 5294-5299.
67. R. Amoroso, G. Cardillo, C. Tomasini, P. Tortoreto, J. Org. Chem. 1992, 57, 1082-1087.
68. Y. N. Belokon, V. I. Bakhmutov, N. I. Chernoglazova, K. A. Kochetkov, S. V. Vitt, N. S. Garbalinskaya, V. M. Belikov, J. Chem. Soc., Perkin Trans. 1 1988, 305-312.
69. A. Studer, D. Seebach, Liebigs Ann. 1995, 217-222.
70. T. M. Zydowsky, E. de Lara, S. G. Spanton, J. Org. Chem. 1990, 55, 5437-5439.
71. The configuration was the result of a comparison of the data obtained for the N-acetylation product of 34c with those reported in the literature for this compound. See: U. Schöllkopf, H.-H. Hausberg, I. Hoppe, M. Segal, U. Reiter, Angew. Chem. 1978, 90, 136-138; Angew. Chem. Int. Ed. Engl. 1978, 17, 117-119.
72. The configuration was the result of a comparison of the data obtained for the N-acetylation product of 34c with those reported in the literature for this compound. See: U. Schöllkopf, H.-H. Hausberg, I. Hoppe, M. Segal, U. Reiter, Angew. Chem. 1978, 90, 136-138; Angew. Chem. Int. Ed. Engl. 1978, 17, 117-119.
73. [4] (compound number 24b). However, in that paper the stereochemical descriptors for position 2 of 24b and for its isomer 24a as well as for their precursors 23a and 23b (position 1) were assigned incorrectly.