Highly regio-, diastereo-, and enantioselective C-H insertions of methyl aryldiazoacetates into cyclic N-BOC-protected amines. Asymmetric synthesis of novel C2-symmetric amines and threo-methylphenidate [7]

Journal of the American Chemical Society

Volumn 121, Issue 27, 1999, Pages 6509-6510

  Davies, Huw M L ^a   Hansen, Tore ^a   Hopper, Darrin W ^a   Panaro, Stephen A ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AMINE; METHYLPHENIDATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; LETTER; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033554039     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9910715     Document Type: Letter

References (27)

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3. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945. (f) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Mol. Catal. 1988, 49, L13. (g) Callott, H. J.; Metz, F. Tetrahedron Lett. 1982, 23, 4321. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
4. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945. (f) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Mol. Catal. 1988, 49, L13. (g) Callott, H. J.; Metz, F. Tetrahedron Lett. 1982, 23, 4321. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
5. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945. (f) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Mol. Catal. 1988, 49, L13. (g) Callott, H. J.; Metz, F. Tetrahedron Lett. 1982, 23, 4321. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
6. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945. (f) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Mol. Catal. 1988, 49, L13. (g) Callott, H. J.; Metz, F. Tetrahedron Lett. 1982, 23, 4321. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
7. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945. (f) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Mol. Catal. 1988, 49, L13. (g) Callott, H. J.; Metz, F. Tetrahedron Lett. 1982, 23, 4321. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
8. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945. (f) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Mol. Catal. 1988, 49, L13. (g) Callott, H. J.; Metz, F. Tetrahedron Lett. 1982, 23, 4321. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
9. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945. (f) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Mol. Catal. 1988, 49, L13. (g) Callott, H. J.; Metz, F. Tetrahedron Lett. 1982, 23, 4321. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
10. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945. (f) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Mol. Catal. 1988, 49, L13. (g) Callott, H. J.; Metz, F. Tetrahedron Lett. 1982, 23, 4321. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
11. Davies, H. M. L. Aldrichim. Acta 1997, 30, 107.
12. Davies, H. M. L.; Hansen, T. J. Am. Chem. Soc. 1997, 119, 9075.
13. The majority of this Communication was presented previously: Davies, H. M. L.; Hodges, L. M.; Hansen, T. Asymmetric synthesis of heterocycles using rhodium-stabilized carbenoids. Abstracts of Papers, 216th National Meeting of the Americal Chemical Society, Boston, MA, August 23-27, 1998; ACS: Washington, DC, 1998; ORGN 254.
14. Davies, H. M. L.; Panaro, S. A. Tetrahedron Lett., submitted.
15. (a) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161.
16. (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
17. (c) Takahata, H.; Kouno, S.; Momose, T. Tetrahedron: Asymmetry 1995, 6, 1085.
18. For racemic syntheses of 4, see: (a) Pannizon, L. Helv. Chim. Acta 1944, 27, 1748. (b) Deutsch, H.; Shi, Q.; Gruaszecka-Kowalik, E.; Schweri, M. J. Med. Chem. 1996, 39, 1201. (c) Axten, J. M.; Krim, L.; Kung, H. F.; Winkler, J. D. J. Org. Chem. 1998, 63, 9628.
19. For racemic syntheses of 4, see: (a) Pannizon, L. Helv. Chim. Acta 1944, 27, 1748. (b) Deutsch, H.; Shi, Q.; Gruaszecka-Kowalik, E.; Schweri, M. J. Med. Chem. 1996, 39, 1201. (c) Axten, J. M.; Krim, L.; Kung, H. F.; Winkler, J. D. J. Org. Chem. 1998, 63, 9628.
20. For racemic syntheses of 4, see: (a) Pannizon, L. Helv. Chim. Acta 1944, 27, 1748. (b) Deutsch, H.; Shi, Q.; Gruaszecka-Kowalik, E.; Schweri, M. J. Med. Chem. 1996, 39, 1201. (c) Axten, J. M.; Krim, L.; Kung, H. F.; Winkler, J. D. J. Org. Chem. 1998, 63, 9628.
21. Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J. Med. Chem. 1998, 41, 591.
22. Prashad, M.; Kim, H.-Y.; Lu, Y.; Liu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750.
23. 1H NMR of the crude amine after extraction and removal of solvent. The yields for 7a,c-e represents the amount of crystalline hydrochloride salt that was obtained after treatment of the crude amine with ethereal HCl. The yield of 7b represented the pure amine after purification by column chromatography. The enantioselectivity was determined by conversion of the crude amine to its trifluoroacetamide derivative, followed by chiral HPLC or GC analysis. The relative stereochemistry of 7c was readily determined by conversion of 7c to a fused β-lactam, in which the cis arrangement of the two protons in the β-lactam ring was assigned on the basis on a distinctive coupling (J = 5.1 Hz) and NOE experiments (Coulton, S.; Gilchrist, T. L.; Graham, K. J. Chem. Soc., Perkin Trans. 1 1998, 1193). The absolute stereochemistry of 7a was determined to be (2S,2′A) using the Mosher amide method developed by Hoye ( Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 8489).
24. 1H NMR of the crude amine after extraction and removal of solvent. The yields for 7a,c-e represents the amount of crystalline hydrochloride salt that was obtained after treatment of the crude amine with ethereal HCl. The yield of 7b represented the pure amine after purification by column chromatography. The enantioselectivity was determined by conversion of the crude amine to its trifluoroacetamide derivative, followed by chiral HPLC or GC analysis. The relative stereochemistry of 7c was readily determined by conversion of 7c to a fused β-lactam, in which the cis arrangement of the two protons in the β-lactam ring was assigned on the basis on a distinctive coupling (J = 5.1 Hz) and NOE experiments (Coulton, S.; Gilchrist, T. L.; Graham, K. J. Chem. Soc., Perkin Trans. 1 1998, 1193). The absolute stereochemistry of 7a was determined to be (2S,2′A) using the Mosher amide method developed by Hoye ( Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 8489).
25. 4 catalyst generates rtireo-methylphenidate in 45% yield and 69% ee.
26. The absolute stereochemistry of 4 and 10 was determined by comparison of the optical rotation with the literature values (ref 10).
27. For examples of intramolecular C-H insertions of aryldiazoacetates into pyrrolines, see: Lim H. J.; Sulikowski, G. A. J. Org. Chem. 1995, 60, 2326.