Stereoselective routes to substituted β-amino carbonyl compounds via heterodiene cycloadditions of an auxiliary-based C2-symmetric ketene acetal

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3501-3504

  Ray, Colin A ^a   Wallace, Timothy W ^a   Ward, Richard A ^b  

^a UNIVERSITY OF SALFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Amino acids and derivatives; Cycloadditions; Diastereoselection; Ketene acetals

Indexed keywords

ACETAL DERIVATIVE; CARBONYL DERIVATIVE; KETENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; DIASTEREOISOMER; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034728950     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00407-X     Document Type: Article

References (24)

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11. For reviews, see: Juaristi, E.; Quintana, D.; Escalante, J. Aldrichimica Acta 1994, 27, 3-11; Cole, D. C. Tetrahedron 1994, 50, 9517-9582; Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117-128; Enantioselective Synthesis of Beta-Amino Acids; Juaristi, E., Ed.; Wiley: New York, 1997. For recent examples, see: Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12-13; Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417; Roche, D.; Prasad, K.; Repic, O. Tetrahedron Lett. 1999, 40, 3665-3668; Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S.-I. Org. Lett. 1999, 1, 107-110; Miyabe, H.; Fujii, K.; Naito, T. Org. Lett. 1999, 1, 569-572.
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13. For reviews, see: Juaristi, E.; Quintana, D.; Escalante, J. Aldrichimica Acta 1994, 27, 3-11; Cole, D. C. Tetrahedron 1994, 50, 9517-9582; Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117-128; Enantioselective Synthesis of Beta-Amino Acids; Juaristi, E., Ed.; Wiley: New York, 1997. For recent examples, see: Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12-13; Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417; Roche, D.; Prasad, K.; Repic, O. Tetrahedron Lett. 1999, 40, 3665-3668; Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S.-I. Org. Lett. 1999, 1, 107-110; Miyabe, H.; Fujii, K.; Naito, T. Org. Lett. 1999, 1, 569-572.
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15. For examples and leading references, see: Tietze, L. F.; Voss, E. Tetrahedron Lett. 1986, 27, 6181-6184; Tietze, L. F.; Hartfiel, U. ibid. 1990, 31, 1697-1700. See also: De Gaudenzi, L.; Apparao, S.; Schmidt, R. R. Tetrahedron 1990, 46, 277-290, and references cited therein.
16. For examples and leading references, see: Tietze, L. F.; Voss, E. Tetrahedron Lett. 1986, 27, 6181-6184; Tietze, L. F.; Hartfiel, U. ibid. 1990, 31, 1697-1700. See also: De Gaudenzi, L.; Apparao, S.; Schmidt, R. R. Tetrahedron 1990, 46, 277-290, and references cited therein.
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20. eq), 3.07 [3.08] (3H, s, NMe), 3.23 [3.21] (3H, s, NMe), 4.40 (1H, ddd, J=2, 5, 12 Hz, 8-Ha), 5.31 (1H, d, J=9 Hz, 4′-H), 5.58 [5.43] (1H, d, J=9 Hz, 5′-H), 6.95-7.10 (2H, m, 3,3′-ArH), 7.15-7.30 (4H, m, 4,4′,5,5′-ArH), 7.50-7.60 (2H, m, 6,6′-ArH), 7.70 [7.62] (1H, d, J=2 Hz, 5-H); 8 (300 MHz) 1.80 (3H, s, ArMe), 1.87 (3H, s, ArMe), 1.92 (3H, s, MeCON), 2.15 (3H, s, 2′-Me), 2.24 (3H, s, 6-Me), 2.60 (1H, dd, J=7, 15 Hz, 2-H), 2.70 (1H, dd, J=7, 15 Hz, 2-H), 4.07 [4.24] (1H, d, J=6 Hz, 4-H), 5.10-5.20 (1H, m, 3-H), 5.24 (1H, d, J=9 Hz, 2′′-H), 6.11 (1H, d, J=9 Hz, 1′′-H), 6.74 (1H, d, J=10 Hz, NH), 6.90-7.00 (2H, m, 3,3′-ArH), 7.07-7.23 (4H, m, 4,4′,5,5′-ArH), 7.46 (1H, br d, J=8 Hz, 6-ArH), 7.60 (1H, br d, J=8 Hz, 6′-ArH).
21. Botta, M.; Saladino, R.; Lamba, D.; Nicoletti, R. Tetrahedron 1993, 49, 6053-6070.
22. 2.
23. The various possible reacting (s-cis) conformations of the heterodiene 2a were generated with CAChe 4.1.1 (Oxford Molecular) and their geometries optimised using an augmented MM3 force field. The results indicate that the H-bonded arrangement depicted in Scheme 2 is>4.9 kcal/mol more stable than the closest alternative.
24. A preliminary crystallographic investigation of a poorly diffracting crystal of 3a has confirmed the gross structure and 4S-configuration depicted.