D-mannitol as the chiral source for the EPC synthesis of both enantiomers of 3-ethoxycarbonyl-4-hydroxy-2-isoxazolines and highly functionalized tricyclic systems

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8235-8246

  Marotta, Emanuela ^a   Baravelli, Marco ^a   Maini, Luigi ^a   Righi, Paolo ^a   Rosini, Goffredo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 ISOXAZOLINE DERIVATIVE; ALDEHYDE DERIVATIVE; MANNITOL;

ARTICLE; CHIRALITY; CYCLIZATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032514851     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980941i     Document Type: Article

References (58)

1. Taken in part from the Tesi di Laurea of L. Maini (March 1997) and M. Baravelli (March 1998) at the Università di Bologna, Facoltà di Chimica Industriale.
2. For a review on biologically active aminopolyols or hydroxylated amino acids, see: Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091. For some other examples, see: (a) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887-7890. (b) Kobayashi, S.; Matsumura, M.; Furuta, T.; Hayashi, T.; Iwamoto, S. Synlett 1997, 301-303. (c) Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta, T.; Matsumura, M. Synlett 1996, 672-674. (d) Mori, K.; Otaka, K. Tetrahedron Lett. 1994, 35, 9207-9210.
3. For a review on biologically active aminopolyols or hydroxylated amino acids, see: Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091. For some other examples, see: (a) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887-7890. (b) Kobayashi, S.; Matsumura, M.; Furuta, T.; Hayashi, T.; Iwamoto, S. Synlett 1997, 301-303. (c) Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta, T.; Matsumura, M. Synlett 1996, 672-674. (d) Mori, K.; Otaka, K. Tetrahedron Lett. 1994, 35, 9207-9210.
4. For a review on biologically active aminopolyols or hydroxylated amino acids, see: Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091. For some other examples, see: (a) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887-7890. (b) Kobayashi, S.; Matsumura, M.; Furuta, T.; Hayashi, T.; Iwamoto, S. Synlett 1997, 301-303. (c) Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta, T.; Matsumura, M. Synlett 1996, 672-674. (d) Mori, K.; Otaka, K. Tetrahedron Lett. 1994, 35, 9207-9210.
5. For a review on biologically active aminopolyols or hydroxylated amino acids, see: Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091. For some other examples, see: (a) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887-7890. (b) Kobayashi, S.; Matsumura, M.; Furuta, T.; Hayashi, T.; Iwamoto, S. Synlett 1997, 301-303. (c) Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta, T.; Matsumura, M. Synlett 1996, 672-674. (d) Mori, K.; Otaka, K. Tetrahedron Lett. 1994, 35, 9207-9210.
6. For a review on biologically active aminopolyols or hydroxylated amino acids, see: Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091. For some other examples, see: (a) Hatakeyama, S.; Yoshida, M.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawamoto, T.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1997, 38, 7887-7890. (b) Kobayashi, S.; Matsumura, M.; Furuta, T.; Hayashi, T.; Iwamoto, S. Synlett 1997, 301-303. (c) Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta, T.; Matsumura, M. Synlett 1996, 672-674. (d) Mori, K.; Otaka, K. Tetrahedron Lett. 1994, 35, 9207-9210.
7. Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447.
8. Henry, L. C. R. Hebd. Seances Acad. Sci. 1895,120, 1265-1268. Rosini, G. The Henry (Nitroaldol) Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 321 and references therein.
9. Henry, L. C. R. Hebd. Seances Acad. Sci. 1895,120, 1265-1268. Rosini, G. The Henry (Nitroaldol) Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 321 and references therein.
10. For an excellent review on the lanthanum-catalysed asymmetric Henry reaction, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256.
11. Studies concerning ab initio models for the nitroaldol (Henry) reaction were reported recently, see: Lecea, B.; Arrieta, A.; Morao, I.; Cossio, F. Chem.-Eur. J. 1997, 3, 20-28.
12. For reviews on the versatility of nitro compounds in organic synthesis, see: (a) Nitro Compounds, Recent Advances in Synthesis and Chemistry; Fever, H., Nielsen, A. T., Eds.; VCH: Weinheim, 1990. (b) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833. (d) Seebach, D.; Colvin, E. W.; Leher, F.; Weller, T. Chimia 1979, 33, 1-18.
13. For reviews on the versatility of nitro compounds in organic synthesis, see: (a) Nitro Compounds, Recent Advances in Synthesis and Chemistry; Fever, H., Nielsen, A. T., Eds.; VCH: Weinheim, 1990. (b) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833. (d) Seebach, D.; Colvin, E. W.; Leher, F.; Weller, T. Chimia 1979, 33, 1-18.
14. For reviews on the versatility of nitro compounds in organic synthesis, see: (a) Nitro Compounds, Recent Advances in Synthesis and Chemistry; Fever, H., Nielsen, A. T., Eds.; VCH: Weinheim, 1990. (b) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833. (d) Seebach, D.; Colvin, E. W.; Leher, F.; Weller, T. Chimia 1979, 33, 1-18.
15. For reviews on the versatility of nitro compounds in organic synthesis, see: (a) Nitro Compounds, Recent Advances in Synthesis and Chemistry; Fever, H., Nielsen, A. T., Eds.; VCH: Weinheim, 1990. (b) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833. (d) Seebach, D.; Colvin, E. W.; Leher, F.; Weller, T. Chimia 1979, 33, 1-18.
16. Rosini, G.; Marotta, E.; Righi, P.; Seerden, J.-P. J. Org. Chem. 1991, 56, 6258-6260.
17. Rosini, G.; Galarini, R.; Marotta, E.; Righi, P. J. Org. Chem. 1990, 55, 781-783.
18. We found that one of the possible IUPAC names of tricyclic compounds of type 1 is ethyl 2,2-dimethyltetrahydro-2H,6bH-1,4,5-trioxa-4a-aza-2-silacyclopenta[cd]pentalene- 6b-carboxylate. (ACD / IUPAC Name, version 3.00; Advanced Chemistry Development, Inc.: Toronto, Nov. 1997.) We suggest the use of the acronym HFTS in place of this awkward IUPAC name.
19. Marotta, E.; Righi, P.; Rosini, G. Tetrahedron Lett. 1998, 39, 1041-1044.
20. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
21. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
22. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
23. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
24. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
25. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
26. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
27. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
28. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
29. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
30. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
31. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
32. Among the classical procedures for the EPC synthesis of 2-hydroxy aldehydes, see: (a) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937-2942. (b) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943-2948. (c) Frye, St. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404. (d) Eliel, E. L. in Asymmetric Synthesis-Stereodifferentiating Addition Reactions; Morrison, J. D., Ed.; Academic Press Inc.: Orlando, FL; Vol. 2. (e) Whitesell, J. K.; Bhattacharya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988-989. (f) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-990. (g) Mukaiyama, T. Tetrahedron 1981, 37, 4111. (h) O'Brien, P.; Warren, S. Tetrahedron Lett. 1995, 36, 2681-2684 and literature therein cited. (i) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702. (j) Dondoni, A. Pure Appl. Chem. 1990, 62, 643-652. (k) Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277. (l) Dondoni, A.; Merino, P. Org. Synth. 1993, 72, 21-31. (m) Kirshning, A.; Dräger, G.; Jung, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255. All these procedures are potentially useful for the preparation of optically active 2-mesyloxy or 2-tosyloxy aldelhydes if the hydrolysis of the corresponding acetals or aminals does not compromise the chemical and/or stereochemical integrity of the products.
33. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon: New York, 1983. 2-Hydroxy aldehydes, O-protected 2-hydroxy aldehydes, as well as 2-mesyloxy and 2-tosyloxy-aldehydes may be obtained by reduction of the methyl or ethyl esters of 2-hydroxy acid derivatives with DIBAH: Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Syntheses; VCH: Weinheim, 1997. Ho, T.-L. Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley & Sons: New York, 1992. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules using Amino Acids; John Wiley & Sons: New York, 1987.
34. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon: New York, 1983. 2-Hydroxy aldehydes, O-protected 2-hydroxy aldehydes, as well as 2-mesyloxy and 2-tosyloxy-aldehydes may be obtained by reduction of the methyl or ethyl esters of 2-hydroxy acid derivatives with DIBAH: Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Syntheses; VCH: Weinheim, 1997. Ho, T.-L. Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley & Sons: New York, 1992. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules using Amino Acids; John Wiley & Sons: New York, 1987.
35. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon: New York, 1983. 2-Hydroxy aldehydes, O-protected 2-hydroxy aldehydes, as well as 2-mesyloxy and 2-tosyloxy-aldehydes may be obtained by reduction of the methyl or ethyl esters of 2-hydroxy acid derivatives with DIBAH: Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Syntheses; VCH: Weinheim, 1997. Ho, T.-L. Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley & Sons: New York, 1992. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules using Amino Acids; John Wiley & Sons: New York, 1987.
36. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon: New York, 1983. 2-Hydroxy aldehydes, O-protected 2-hydroxy aldehydes, as well as 2-mesyloxy and 2-tosyloxy-aldehydes may be obtained by reduction of the methyl or ethyl esters of 2-hydroxy acid derivatives with DIBAH: Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Syntheses; VCH: Weinheim, 1997. Ho, T.-L. Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley & Sons: New York, 1992. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules using Amino Acids; John Wiley & Sons: New York, 1987.
37. 4 is reported to reduce 4-hydroxy-2-isoxazolines to aminopolyols by introduction of the hydride ion syn to the C4 hydroxyl group and anti when this has been protected with a group bulky enough: Jäger, V.; Schwab, W.; Buss, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 601-603.
38. Jäger et al. have shown 4-hydroxy-2-isoxazolines are versatile intermediates for the synthesis of amino sugars and other biologically important molecules, see: (a) Jäger, V.; Schone, R. Tetrahedron 1984, 40, 2199-2210. (b) Jäger, V.; Müller, I.; Schohe, R.; Frey, M.; Ehrler, R.; Häfele, B.; Schröter, D. Lect. Heter. Chem. 1985, 6, 79-98 and references therein.
39. Jäger et al. have shown 4-hydroxy-2-isoxazolines are versatile intermediates for the synthesis of amino sugars and other biologically important molecules, see: (a) Jäger, V.; Schone, R. Tetrahedron 1984, 40, 2199-2210. (b) Jäger, V.; Müller, I.; Schohe, R.; Frey, M.; Ehrler, R.; Häfele, B.; Schröter, D. Lect. Heter. Chem. 1985, 6, 79-98 and references therein.
40. Le Merrer, Y.; Duréault, A.; Greck, C.; Micos-Lauguin, D.; Gravier, G.; Depazay, J. C. Heterocycles 1987, 25, 541-548.
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42. (b) Tranchpain, I.; Le Berre, F.; Duréault, A.; Le Merrer, Y.; Depazay, J. C. Tetrahedron 1989, 45, 2057-2065.
43. (c) Allevi, P.; Anastaaia, M.; Ciuffreda, P.; Sanvito, A. M. Tetrahedron: Asymmetry 1994, 5, 927-934.
44. House, H. O.; Chu, C. Y.; Wilkins, J. M.; Umen, M. J. Org. Chem. 1975, 40, 1460-1469.
45. Morpain, C.; Tisserand, M. J. Chem. Soc., Perkin Trans. 1 1979, 1379-1383.
46. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
47. (b) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143. For a more recent application with high-field FT NMR, see: Ohtani, I.; Jusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
48. (b) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143. For a more recent application with high-field FT NMR, see: Ohtani, I.; Jusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
49. For a more detailed discussion see the Supporting Information.
50. For more details and actual chromatograms, see the Experimental Section and Supporting Information.
51. For methods that yield optically active 4-hydroxy-2-isoxazolines, see: (a) Liu, J.; Eddings, A.; Wallace, R. H. Tetrahedron Lett. 1997, 38, 6795-6798. (b) Wade, P. A.; Shah, S. S.; Govindarajian, J. Org. Chem. 1994, 59, 7199-7200. (c) Davis, F. A.; Kumar, A.; Reddy, R. E.; Chen, B.; Wade, P. A.; Shah, S. W. J. Org. Chem. 1993, 58, 7591-7593. (d) Panek, J. S.; Beresis, R. T. J. Am. Chem. Soc. 1993, 115, 7898-7899.
52. For methods that yield optically active 4-hydroxy-2-isoxazolines, see: (a) Liu, J.; Eddings, A.; Wallace, R. H. Tetrahedron Lett. 1997, 38, 6795-6798. (b) Wade, P. A.; Shah, S. S.; Govindarajian, J. Org. Chem. 1994, 59, 7199-7200. (c) Davis, F. A.; Kumar, A.; Reddy, R. E.; Chen, B.; Wade, P. A.; Shah, S. W. J. Org. Chem. 1993, 58, 7591-7593. (d) Panek, J. S.; Beresis, R. T. J. Am. Chem. Soc. 1993, 115, 7898-7899.
53. For methods that yield optically active 4-hydroxy-2-isoxazolines, see: (a) Liu, J.; Eddings, A.; Wallace, R. H. Tetrahedron Lett. 1997, 38, 6795-6798. (b) Wade, P. A.; Shah, S. S.; Govindarajian, J. Org. Chem. 1994, 59, 7199-7200. (c) Davis, F. A.; Kumar, A.; Reddy, R. E.; Chen, B.; Wade, P. A.; Shah, S. W. J. Org. Chem. 1993, 58, 7591-7593. (d) Panek, J. S.; Beresis, R. T. J. Am. Chem. Soc. 1993, 115, 7898-7899.
54. For methods that yield optically active 4-hydroxy-2-isoxazolines, see: (a) Liu, J.; Eddings, A.; Wallace, R. H. Tetrahedron Lett. 1997, 38, 6795-6798. (b) Wade, P. A.; Shah, S. S.; Govindarajian, J. Org. Chem. 1994, 59, 7199-7200. (c) Davis, F. A.; Kumar, A.; Reddy, R. E.; Chen, B.; Wade, P. A.; Shah, S. W. J. Org. Chem. 1993, 58, 7591-7593. (d) Panek, J. S.; Beresis, R. T. J. Am. Chem. Soc. 1993, 115, 7898-7899.
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