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Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
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Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
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Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
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Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
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0030821811
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Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
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0037182202
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N-Protected α-amino aldehydes have been used in Passerini reactions: (a) Banfi, L.; Guanti, G.; Riva, R.; Basso, A.; Calcagno, E. Tetrahedron Lett. 2002, 43, 4067. (b) Owens, T. D.; Araldi, G. L.; Nutt, R. F.; Semple, E. Tetrahedron Lett. 2001, 42, 6271.
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N-Protected α-amino aldehydes have been used in Passerini reactions: (a) Banfi, L.; Guanti, G.; Riva, R.; Basso, A.; Calcagno, E. Tetrahedron Lett. 2002, 43, 4067. (b) Owens, T. D.; Araldi, G. L.; Nutt, R. F.; Semple, E. Tetrahedron Lett. 2001, 42, 6271.
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48
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0042286502
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note
-
Conversion to amino acids 8 in two steps involving the formation of the corresponding amino aldehydes as intermediates (Swern oxidation then TEMPO-BAIB) disappointingly gave decomposed products.
-
-
-
-
49
-
-
0027205552
-
-
The oxidation of DHPM and dihydropyridine (DHP) derivatives is an issue that has been addressed by several authors. Dealkylation (in addition to aromatization) usually occurs when the DHPM and DHP rings bear a secondary alkyl group at the C4 position while dehydrogenation takes place in the presence of a primary alkyl group at the same position. This is a general trend in the oxidation of DHPMs and DHPs and it is explained by a sequence proceeding by a hydride abstraction in the first step. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Slavinskaya, V. A.; Duburs, G.; Sile, D.; Kreile, D.; Khanina, E. L. USSR Patent 632,695, 1978. (c) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 3, 463. (d) Böcker, R. H.; Guengerich F. P. J. Med. Chem. 1986, 29, 1596.
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Kappe, C.O.1
-
50
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0042787592
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USSR Patent 632,695, 1978
-
The oxidation of DHPM and dihydropyridine (DHP) derivatives is an issue that has been addressed by several authors. Dealkylation (in addition to aromatization) usually occurs when the DHPM and DHP rings bear a secondary alkyl group at the C4 position while dehydrogenation takes place in the presence of a primary alkyl group at the same position. This is a general trend in the oxidation of DHPMs and DHPs and it is explained by a sequence proceeding by a hydride abstraction in the first step. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Slavinskaya, V. A.; Duburs, G.; Sile, D.; Kreile, D.; Khanina, E. L. USSR Patent 632,695, 1978. (c) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 3, 463. (d) Böcker, R. H.; Guengerich F. P. J. Med. Chem. 1986, 29, 1596.
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Slavinskaya, V.A.1
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Khanina, E.L.5
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51
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0026530628
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-
The oxidation of DHPM and dihydropyridine (DHP) derivatives is an issue that has been addressed by several authors. Dealkylation (in addition to aromatization) usually occurs when the DHPM and DHP rings bear a secondary alkyl group at the C4 position while dehydrogenation takes place in the presence of a primary alkyl group at the same position. This is a general trend in the oxidation of DHPMs and DHPs and it is explained by a sequence proceeding by a hydride abstraction in the first step. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Slavinskaya, V. A.; Duburs, G.; Sile, D.; Kreile, D.; Khanina, E. L. USSR Patent 632,695, 1978. (c) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 3, 463. (d) Böcker, R. H.; Guengerich F. P. J. Med. Chem. 1986, 29, 1596.
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Eynde, J.J.V.1
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Maquestiau, A.3
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52
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0022550688
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The oxidation of DHPM and dihydropyridine (DHP) derivatives is an issue that has been addressed by several authors. Dealkylation (in addition to aromatization) usually occurs when the DHPM and DHP rings bear a secondary alkyl group at the C4 position while dehydrogenation takes place in the presence of a primary alkyl group at the same position. This is a general trend in the oxidation of DHPMs and DHPs and it is explained by a sequence proceeding by a hydride abstraction in the first step. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Slavinskaya, V. A.; Duburs, G.; Sile, D.; Kreile, D.; Khanina, E. L. USSR Patent 632,695, 1978. (c) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 3, 463. (d) Böcker, R. H.; Guengerich F. P. J. Med. Chem. 1986, 29, 1596.
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Böcker, R.H.1
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0042286501
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note
-
Each step occurred in fair yield (benzylation, 65%; hydrolysis, 50%) but after column chromatography it was possible to recover monobenzylated (benzylation step) and dibenzylated (hydrolysis step) derivatives of 4 that were reused in appropriate reactions of Scheme 1.
-
-
-
-
54
-
-
0043288667
-
-
note
-
One-step oxidative cleavage of the oxazolidine ring with the Jones reagent (see ref 14a,b) afforded the corresponding amino acid in lower overall yield.
-
-
-
-
55
-
-
0043288663
-
-
note
-
A different protection strategy based on selective N3 acylation (acetyl and pivaloyl groups) of cycloadducts 4 was also investigated to allow a higher yielding deprotection to 8. Unfortunately, N,O-acyl migration occurred during acetonide removal of N-acyl cycloadducts affording undesired O-acyl derivatives of 5.
-
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-
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56
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0041785447
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note
-
The use of the Jones reagent gave a lower yield (ca. 50%) of N′-Boc amino acid 29.
-
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60
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0242560405
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Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
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