Engineering acyclic stereocontrol in the alkylation of vinylglycine- derived dianions: Asymmetric synthesis of higher α-vinyl amino acids

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 2907-2918

  Berkowitz, David B ^a   McFadden, Jill M ^a   Sloss, Marianne K ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; VINYL DERIVATIVE;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; CHELATION; CONFORMATION; STEREOCHEMISTRY;

ALKYLATION; AMINO ACIDS; ENZYME INHIBITORS; GLYCINE; HYDROLYSIS; INDICATORS AND REAGENTS; PYRIDOXAL PHOSPHATE; TEMPERATURE; VINYL COMPOUNDS;

EID: 0034685731     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9918091     Document Type: Article

References (78)

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27. Recent references include: (a) Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105-6108. (b) Wenglowsky, S.; Hegedus, L. S. J. Am. Chem. Soc. 1998, 120, 12468-12473. Meyer, L.; Poirier, J. M.; Duhamel, P.; Duhamel, L. J. Org. Chem. 1998, 63, 8094-8095. Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (e) Juaristi, E.; Lopez-Ruiz, H.; Madrigal, D.; Ramirez-Quiros, Y.; Escalante, J. J. Org. Chem. 1998, 63, 4706-4710. (f) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Najera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995-997. (g) Ohfune, Y.; Moon, S.-H.; Horikawa, M. Pure Appl. Chem. 1996, 68, 645-648. (h) Ferey, V.; Tuopet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7, 7379-7388.
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29. Recent references include: (a) Belokon, Y. N.; North, M.; Kublitski, V. S.; Ikonnikov, N. S.; Krasik, P. E.; Maleev, V. I. Tetrahedron Lett. 1999, 40, 6105-6108. (b) Wenglowsky, S.; Hegedus, L. S. J. Am. Chem. Soc. 1998, 120, 12468-12473. Meyer, L.; Poirier, J. M.; Duhamel, P.; Duhamel, L. J. Org. Chem. 1998, 63, 8094-8095. Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (e) Juaristi, E.; Lopez-Ruiz, H.; Madrigal, D.; Ramirez-Quiros, Y.; Escalante, J. J. Org. Chem. 1998, 63, 4706-4710. (f) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Najera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995-997. (g) Ohfune, Y.; Moon, S.-H.; Horikawa, M. Pure Appl. Chem. 1996, 68, 645-648. (h) Ferey, V.; Tuopet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7, 7379-7388.
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56. 24b In the case of the "exo-extended" dienolate working model presented here, it is conceivable that dispersion forces could lead to a favorable face-to-face interaction, particularly as the system approaches an alkylation transition state in which charge is becoming more widely dispersed.
57. For a pioneering example of the use of the 8-phenylmenthyl auxiliary in an asymmetric Diels-Alder reaction, see: Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908-6909.
58. For reviews on the postulated use of π-π interactions in asymmetric organic synthesis, see: (a) Dumas, F.; Mezrhab, B.; d'Angelo, J. J. Org. Chem. 1996, 61, 2293-2304. (b) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. Whitesell, J. K. Chem. Rev. 1992, 92, 953-964.
59. For reviews on the postulated use of π-π interactions in asymmetric organic synthesis, see: (a) Dumas, F.; Mezrhab, B.; d'Angelo, J. J. Org. Chem. 1996, 61, 2293-2304. (b) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. Whitesell, J. K. Chem. Rev. 1992, 92, 953-964.
60. For reviews on the postulated use of π-π interactions in asymmetric organic synthesis, see: (a) Dumas, F.; Mezrhab, B.; d'Angelo, J. J. Org. Chem. 1996, 61, 2293-2304. (b) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. Whitesell, J. K. Chem. Rev. 1992, 92, 953-964.
61. (a) Meyer, L.; Poirier, J.-M.; Duhamel, P.; Duhamel, L. J. Org. Chem. 1998, 63, 8094-8095.
62. (b) Swindell, C. S.; Tao, M. J. Org. Chem. 1993, 58, 5889-5891.
63. (c) Ojima, I.; Habus, I.; Zhao, M.; George, G.; Jayasinghe, L. R. J. Org. Chem. 1991, 56, 1681-1683.
64. For a general discussion on factors influencing π-π interactions, see: Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
65. (a) Cozzi, F.; Cinquini, M.; Annuziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331.
66. (b) Muehldorf, A. V.; Van Engen D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561-6562.
67. (a) Williams, V. E.; Lemieux, R. P. J. Am. Chem. Soc. 1998, 120, 11311-11315.
68. (b) Askew, B.; Ballester, P.; Buhr, C.; Jeong, K. S.; Jones, S.; Parris, K.; Williams, K.; Rebek, J., Jr. J. Am. Chem. Soc. 1989, 111, 1082-1090.
69. The MacSpartan Plus (version 1.1.9) package (Wavefunction, Inc., Irvine, CA 92612) was used for all geometry optimizations. Complete tables of atomic Cartesian coordinates, atomic partial charges, calculated dipole moments and heats of formation for each of the conformers I-IV are available upon request.
70. a-alkylations in these dianionic dienolate systems were found to be most successful if, following initial deprotonation with LDA, two equivalents of n-BuLi were employed for the second deprotonation. Presumably, the first equivalent of n-BuLi is required to deprotonate the diisopropylamine that is formed in the initial deprotonation reaction.
71. 1′ bond.
72. Of course, by the Curtin-Hammett principle, if under the reaction conditions, the interconversion of conformers I and II, say, were fast relative to their transformation to products, the product distribution would be governed by the relative energies of the transition states leading to the products, rather than by the relative energies of I and II. In such a situation, conformational prefererences in the transition states need not directly reflect ground state conformational preferences.
73. 22 Thus the atom-to-atom distances we obtain using the MacSpartan Plus program slightly overestimate the distance between the two π-surfaces.
74. Gassman, P. G.; Schenk, W. N. J. Org. Chem. 1977, 42, 918-920.
75. For a related Lys side chain elaboration, see: Danzin, C.; Casara, P.; Claverie, N.; Metcalf, B. W. J. Med. Chem. 1981, 24, 16-20.
76. Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656-4661.
77. Winkle, M. R.; Lansinger, J. M.; Ronald, R. C. J. Chem. Soc., Chem. Commun. 1980, 87-88.
78. Marshall, J. L. Carbon-Carbon and Carbon-Proton NMR Couplings: Applications to Organic Stereochemistry and Conformational Analysis (Verlag Chemie International, 1983) pp 35-38.