Synthetic applications of lithiated N-Boc allylic amines as asymmetric homoenolate equivalents

Journal of Organic Chemistry

Volumn 68, Issue 4, 2003, Pages 1207-1215

  Whisler, Marna C ^a   Beak, Peter ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOGENIC CENTERS;

ACIDIZATION; ALDEHYDES; AMINES; AROMATIC COMPOUNDS; HYDROLYSIS; SYNTHESIS (CHEMICAL);

LITHIUM COMPOUNDS;

2 FORMYL 4 PHENYL 1 AMINOCYCLOPENTANE; ALDEHYDE; ALKENE; ALLYL COMPOUND; BETA LACTAM; CARBAMIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; NITRONE; SPARTEINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLOADDITION; DIASTEREOISOMER; ENANTIOSELECTIVITY; HYDROLYSIS; LITHIATION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALDEHYDES; ALLYL COMPOUNDS; AMINES; CARBAMATES; CATALYSIS; CHEMISTRY, ORGANIC; CYCLOPENTANES; LACTAMS; LITHIUM; MOLECULAR STRUCTURE; SPARTEINE; STEREOISOMERISM;

EID: 0037458863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0260084     Document Type: Article

References (52)

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24. Chiral β-lactams are of considerable interest, as many pharmacologically active compounds contain this framework. See: Antibiotics Containing the β-Lactam Structure; Morin, R. B., Goldman, M., Eds.; Academic Press: New York, 1983; Vols. 1-3. Recent efforts for efficient asymmetric syntheses of azetidin-2-ones have concentrated on stereoselective ketene-imine cycloadditions and ester enolateimine condensations. See: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223-3225. (b) Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2000, 563-572.
25. Chiral β-lactams are of considerable interest, as many pharmacologically active compounds contain this framework. See: Antibiotics Containing the β-Lactam Structure; Morin, R. B., Goldman, M., Eds.; Academic Press: New York, 1983; Vols. 1-3. Recent efforts for efficient asymmetric syntheses of azetidin-2-ones have concentrated on stereoselective ketene-imine cycloadditions and ester enolateimine condensations. See: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223-3225. (b) Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2000, 563-572.
26. 2O were unsuccessful.
27. Cispentacin has recently been isolated from Bacillus cereus and Streptomyces setonii and shown to have potent activity as an antifungal antibiotic in mice. See: (a) Konishi, M.; Nishio, M.; Saitoh, T.; Miyaki, T.; Oki, T.; Kawaguchi, H. J. Antibiot. 1989, 42, 1749-1755. (b) Oki, T.; Hirano, M.; Tomatsu, K.; Numata, K.; Kamei, H. J. Antibiot. 1989, 42, 1756-1762. (c) Iwamoto, T.; Tsujii, E.; Ezaki, M.; Fujie, A.; Hashimoto, S.; Okuhara, M.; Kohsaka, M.; Imanaka, H. J. Antibiot. 1990, 43, 1-7. (d) Kawabata, K.; Inamoto, Y.; Sakane, K. J. Antibiot. 1990, 43, 513-518. Cispentacin is a compound of synthetic interest: (e) Fülöp, F.; Palkó, M.; Kámán, J.; Lázár, L.; Sillanpää, R. Tetrahedron: Asymmetry 2000, 11, 4179-4187. (f) Aggarwal, V. K.; Roseblade, S. J.; Barrell, J. K.; Alexander, R. Org. Lett. 2002, 7, 1227-1229.
28. Cispentacin has recently been isolated from Bacillus cereus and Streptomyces setonii and shown to have potent activity as an antifungal antibiotic in mice. See: (a) Konishi, M.; Nishio, M.; Saitoh, T.; Miyaki, T.; Oki, T.; Kawaguchi, H. J. Antibiot. 1989, 42, 1749-1755. (b) Oki, T.; Hirano, M.; Tomatsu, K.; Numata, K.; Kamei, H. J. Antibiot. 1989, 42, 1756-1762. (c) Iwamoto, T.; Tsujii, E.; Ezaki, M.; Fujie, A.; Hashimoto, S.; Okuhara, M.; Kohsaka, M.; Imanaka, H. J. Antibiot. 1990, 43, 1-7. (d) Kawabata, K.; Inamoto, Y.; Sakane, K. J. Antibiot. 1990, 43, 513-518. Cispentacin is a compound of synthetic interest: (e) Fülöp, F.; Palkó, M.; Kámán, J.; Lázár, L.; Sillanpää, R. Tetrahedron: Asymmetry 2000, 11, 4179-4187. (f) Aggarwal, V. K.; Roseblade, S. J.; Barrell, J. K.; Alexander, R. Org. Lett. 2002, 7, 1227-1229.
29. Cispentacin has recently been isolated from Bacillus cereus and Streptomyces setonii and shown to have potent activity as an antifungal antibiotic in mice. See: (a) Konishi, M.; Nishio, M.; Saitoh, T.; Miyaki, T.; Oki, T.; Kawaguchi, H. J. Antibiot. 1989, 42, 1749-1755. (b) Oki, T.; Hirano, M.; Tomatsu, K.; Numata, K.; Kamei, H. J. Antibiot. 1989, 42, 1756-1762. (c) Iwamoto, T.; Tsujii, E.; Ezaki, M.; Fujie, A.; Hashimoto, S.; Okuhara, M.; Kohsaka, M.; Imanaka, H. J. Antibiot. 1990, 43, 1-7. (d) Kawabata, K.; Inamoto, Y.; Sakane, K. J. Antibiot. 1990, 43, 513-518. Cispentacin is a compound of synthetic interest: (e) Fülöp, F.; Palkó, M.; Kámán, J.; Lázár, L.; Sillanpää, R. Tetrahedron: Asymmetry 2000, 11, 4179-4187. (f) Aggarwal, V. K.; Roseblade, S. J.; Barrell, J. K.; Alexander, R. Org. Lett. 2002, 7, 1227-1229.
30. Cispentacin has recently been isolated from Bacillus cereus and Streptomyces setonii and shown to have potent activity as an antifungal antibiotic in mice. See: (a) Konishi, M.; Nishio, M.; Saitoh, T.; Miyaki, T.; Oki, T.; Kawaguchi, H. J. Antibiot. 1989, 42, 1749-1755. (b) Oki, T.; Hirano, M.; Tomatsu, K.; Numata, K.; Kamei, H. J. Antibiot. 1989, 42, 1756-1762. (c) Iwamoto, T.; Tsujii, E.; Ezaki, M.; Fujie, A.; Hashimoto, S.; Okuhara, M.; Kohsaka, M.; Imanaka, H. J. Antibiot. 1990, 43, 1-7. (d) Kawabata, K.; Inamoto, Y.; Sakane, K. J. Antibiot. 1990, 43, 513-518. Cispentacin is a compound of synthetic interest: (e) Fülöp, F.; Palkó, M.; Kámán, J.; Lázár, L.; Sillanpää, R. Tetrahedron: Asymmetry 2000, 11, 4179-4187. (f) Aggarwal, V. K.; Roseblade, S. J.; Barrell, J. K.; Alexander, R. Org. Lett. 2002, 7, 1227-1229.
31. Cispentacin has recently been isolated from Bacillus cereus and Streptomyces setonii and shown to have potent activity as an antifungal antibiotic in mice. See: (a) Konishi, M.; Nishio, M.; Saitoh, T.; Miyaki, T.; Oki, T.; Kawaguchi, H. J. Antibiot. 1989, 42, 1749-1755. (b) Oki, T.; Hirano, M.; Tomatsu, K.; Numata, K.; Kamei, H. J. Antibiot. 1989, 42, 1756-1762. (c) Iwamoto, T.; Tsujii, E.; Ezaki, M.; Fujie, A.; Hashimoto, S.; Okuhara, M.; Kohsaka, M.; Imanaka, H. J. Antibiot. 1990, 43, 1-7. (d) Kawabata, K.; Inamoto, Y.; Sakane, K. J. Antibiot. 1990, 43, 513-518. Cispentacin is a compound of synthetic interest: (e) Fülöp, F.; Palkó, M.; Kámán, J.; Lázár, L.; Sillanpää, R. Tetrahedron: Asymmetry 2000, 11, 4179-4187. (f) Aggarwal, V. K.; Roseblade, S. J.; Barrell, J. K.; Alexander, R. Org. Lett. 2002, 7, 1227-1229.
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