Observations concerning the existence and reactivity of free α-amino aldehydes as chemical intermediates: Evidence for epimerization-free adduct formation with various nucleophiles [11]

Journal of the American Chemical Society

Volumn 122, Issue 13, 2000, Pages 3236-3237

  Myers, Andrew G ^a   Kung, Daniel W ^a   Zhong, Boyu ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; NITRILE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLOGRAPHY; DERIVATIZATION; DIMERIZATION; LETTER; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0034607293     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000136x     Document Type: Letter

References (17)

1. Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828-10829.
2. Fischer, E. Chem. Ber. 1908, 41, 1019-1023.
3. Adams successfully prepared optically active histidinal by Fischer's method: Adams, E. J. Biol. Chem. 1955, 217, 317-324. See also: Bullerwell, R. A. F.; Lawson, A. J. Chem. Soc. 1951, 3030-3032. 2-Deoxy-2-amino sugars are formally derivatives of α-amino aldehydes but are not included as part of this discussion,
4. Adams successfully prepared optically active histidinal by Fischer's method: Adams, E. J. Biol. Chem. 1955, 217, 317-324. See also: Bullerwell, R. A. F.; Lawson, A. J. Chem. Soc. 1951, 3030-3032. 2-Deoxy-2-amino sugars are formally derivatives of α-amino aldehydes but are not included as part of this discussion,
5. Nenitzescu, C. D. Chimie Organica; Editura Didactica: Bucharest, Romania, 1968; p 716.
6. Myers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359-1362.
7. a of the protonated amino group is estimated to be 8, using 2-deoxy-2-amino D-glucose as a reference: Blasko, A.; Bunton, C. A.; Bunel, S.; Ibarra, C.; Moraga, E. Carbohydr. Res. 1997, 298, 163-172.
8. 9 using N-Fmoc-protective groups.
9. There is a marked solvent effect in the reaction of 7 with morpholine. In the protic solvent trifluoroethanol. Strecker reaction occcurs without Fmoc cleavage. In the dipolar aprotic solvent DMF, cleavage of the Fmoc group occurs without competing Strecker condensation.
10. Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401-8402.
11. The facility with which N-protected α-amino aldehydes epimerize is well documented. For reviews of N-protected α-amino aldehydes as synthetic intermediates, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. (b) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399-484. (c) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546. (d) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872. (e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162. Strategies to minimize the epimerization of N-protected α-amino aldehydes include Rapoport's 9-(9-phenylfluorenyl) substitution of the α-amino group. (f) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 236-239, and Reetz' N,N-dibenzyl derivatization: (g) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
12. The facility with which N-protected α-amino aldehydes epimerize is well documented. For reviews of N-protected α-amino aldehydes as synthetic intermediates, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. (b) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399-484. (c) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546. (d) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872. (e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162. Strategies to minimize the epimerization of N-protected α-amino aldehydes include Rapoport's 9-(9-phenylfluorenyl) substitution of the α-amino group. (f) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 236-239, and Reetz' N,N-dibenzyl derivatization: (g) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
13. The facility with which N-protected α-amino aldehydes epimerize is well documented. For reviews of N-protected α-amino aldehydes as synthetic intermediates, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. (b) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399-484. (c) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546. (d) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872. (e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162. Strategies to minimize the epimerization of N-protected α-amino aldehydes include Rapoport's 9-(9-phenylfluorenyl) substitution of the α-amino group. (f) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 236-239, and Reetz' N,N-dibenzyl derivatization: (g) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
14. The facility with which N-protected α-amino aldehydes epimerize is well documented. For reviews of N-protected α-amino aldehydes as synthetic intermediates, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. (b) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399-484. (c) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546. (d) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872. (e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162. Strategies to minimize the epimerization of N-protected α-amino aldehydes include Rapoport's 9-(9-phenylfluorenyl) substitution of the α-amino group. (f) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 236-239, and Reetz' N,N-dibenzyl derivatization: (g) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
15. The facility with which N-protected α-amino aldehydes epimerize is well documented. For reviews of N-protected α-amino aldehydes as synthetic intermediates, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. (b) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399-484. (c) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546. (d) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872. (e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162. Strategies to minimize the epimerization of N-protected α-amino aldehydes include Rapoport's 9-(9-phenylfluorenyl) substitution of the α-amino group. (f) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 236-239, and Reetz' N,N-dibenzyl derivatization: (g) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
16. The facility with which N-protected α-amino aldehydes epimerize is well documented. For reviews of N-protected α-amino aldehydes as synthetic intermediates, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. (b) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399-484. (c) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546. (d) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872. (e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162. Strategies to minimize the epimerization of N-protected α-amino aldehydes include Rapoport's 9-(9-phenylfluorenyl) substitution of the α-amino group. (f) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 236-239, and Reetz' N,N-dibenzyl derivatization: (g) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
17. The facility with which N-protected α-amino aldehydes epimerize is well documented. For reviews of N-protected α-amino aldehydes as synthetic intermediates, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. (b) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399-484. (c) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546. (d) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872. (e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162. Strategies to minimize the epimerization of N-protected α-amino aldehydes include Rapoport's 9-(9-phenylfluorenyl) substitution of the α-amino group. (f) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 236-239, and Reetz' N,N-dibenzyl derivatization: (g) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.