1,3-Asymmetric induction via 1,5-hydrogen atom translocation reactions. Highly enantioselective synthesis of β-substituted β-amino acids

Journal of the American Chemical Society

Volumn 118, Issue 36, 1996, Pages 8727-8728

  Beaulieu, F ^a   Arora, J ^a   Veith, U ^a   Taylor, N J ^a   Chapell, B J ^a   Snieckus, V ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BETA AMINO ACID; PYRIMIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029794036     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961484v     Document Type: Article

References (33)

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11. Beaulieu, F. Ph.D. Thesis, University of Waterloo, 1994. Arora, J. M.Sc. Thesis, University of Waterloo, 1995.
12. For an alternative method of generating α-amidoyl radicals via 1,5-hydrogen atom translocation, see: Esker, J. L.; Newcomb, M. Tetrahedron Lett. 1992, 33, 5913-5916. Esker, J. L.; Newcomb, M. J. Org. Chem. 1994, 59, 2779-2786. For radical C-C bond formation by photoinduced electron transfer in α-silyl carbamates, see: Meggers, E.; Steckhan, E.; Blechert, S. Angew. Chem., Int, Ed. Engl. 1995, 34, 2137-2139. Pandey, G.; Reddy, G. D.; Chakrabarti, D. J. Chem. Soc., Perkin Trans, 1 1996, 219-224.
13. For an alternative method of generating α-amidoyl radicals via 1,5-hydrogen atom translocation, see: Esker, J. L.; Newcomb, M. Tetrahedron Lett. 1992, 33, 5913-5916. Esker, J. L.; Newcomb, M. J. Org. Chem. 1994, 59, 2779-2786. For radical C-C bond formation by photoinduced electron transfer in α-silyl carbamates, see: Meggers, E.; Steckhan, E.; Blechert, S. Angew. Chem., Int, Ed. Engl. 1995, 34, 2137-2139. Pandey, G.; Reddy, G. D.; Chakrabarti, D. J. Chem. Soc., Perkin Trans, 1 1996, 219-224.
14. For an alternative method of generating α-amidoyl radicals via 1,5-hydrogen atom translocation, see: Esker, J. L.; Newcomb, M. Tetrahedron Lett. 1992, 33, 5913-5916. Esker, J. L.; Newcomb, M. J. Org. Chem. 1994, 59, 2779-2786. For radical C-C bond formation by photoinduced electron transfer in α-silyl carbamates, see: Meggers, E.; Steckhan, E.; Blechert, S. Angew. Chem., Int, Ed. Engl. 1995, 34, 2137-2139. Pandey, G.; Reddy, G. D.; Chakrabarti, D. J. Chem. Soc., Perkin Trans, 1 1996, 219-224.
15. For an alternative method of generating α-amidoyl radicals via 1,5-hydrogen atom translocation, see: Esker, J. L.; Newcomb, M. Tetrahedron Lett. 1992, 33, 5913-5916. Esker, J. L.; Newcomb, M. J. Org. Chem. 1994, 59, 2779-2786. For radical C-C bond formation by photoinduced electron transfer in α-silyl carbamates, see: Meggers, E.; Steckhan, E.; Blechert, S. Angew. Chem., Int, Ed. Engl. 1995, 34, 2137-2139. Pandey, G.; Reddy, G. D.; Chakrabarti, D. J. Chem. Soc., Perkin Trans, 1 1996, 219-224.
16. For 1,2-asymmetric induction via radical intervention, see: Curran, D. P.; Abraham, A. C. Tetrahedron 1993, 49, 4821-4840.
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19. β-Alanine was converted into its N-methylamide, which was condensed with pivaldehyde to give the Schiff base. Treatment with 2-bromo/ iodobenzoic anhydride in Tol at reflux gave heterocyles 1a and 1b in 31% and 21% overall yield, respectively.
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25. 9a In the overall conversion of asparagine into this product, we detected (NMR) and isolated only the cis isomer.
26. -1, F(000) = 364, T = 295 K. Data were collected on a Siemens P4 diffractometer with Mo Kα radiation (λ = 0.71073 Å). 3130 reflections were measured giving 2914 independent reflections (1457 Friedel pairs). The structure was solved using Patterson and Fourier routines (SHELXTL Ver.4.2/IRIS) and refined by full-matrix least-squares on F resulting in final R, wR, and GoF (for 2288 data with F > 4.0σ(F)) of 0.0367, 0.0260, and 1.78, respectively, for solution using the S model (for solution of the R model, final R, and wR values were 0.0675 and 0,0642, respectively).
27. Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradón, B.; Hidber, P. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mouriño, A.; Pfammatter, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stucky, G.; Petter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molins, E. Helv. Chim. Acta 1992, 75, 913-934.
28. 2H NMR spectra (30.7 MHz).
29. 6 exhibits four resonances for the tert-butyl group at 20 °C (for details, see supporting information). We believe that the split in the major and minor resonances, e.g. at 20 °C, is due to restricted rotation about the Ar-C(O) bond, and the major and minor resonances themselves, e.g. at 60 °C. are due to the Z:E amide isomerization of (O)C-N bond. At 80 °C, the integration of the major and the minor peaks correspond to a ratio of 7:3. Overall coalescence is observed at 100 °C (ΔG‡ = 18.7 kcal/mol).
30. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
31. An (S,S)-Whelk-O1 chiral column was used. Enantiomeric purity assays were completed with both racemic and enantioenriched materials and repeated at least once in order to ensure accuracy of the method used. For details, see supporting information.
32. Obtained from Sigma/Aldrich as the racemate.
33. For the synthesis and biological properties of amino sulfonic acids, see e.g.: Braghiroli, D.; Mussati, E.; Di Bella, M.; Saladini, M. Tetrahedron: Asymmetry 1996, 7, 831-836 and references cited therein.