Enantiomerically Pure 3-Substituted 2-Phenylprolines by Caesium Fluoride / Tetramethoxysilane Mediated 1,4- Addition of 3(S)-5(R)-Diphenylmorpholin-2-one to Acrylates

Synlett

Volumn 1997, Issue 8, 1997, Pages 935-938

  Harwood, Laurence M ^a   Hamblett, Giles ^b   Jiménez Díaz, Antonio I ^b,c   Watkin, David J ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0342855958     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-947     Document Type: Article

References (30)

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2. For example see: Duthaler, R. O. Tetrahedron, 1994, 50, 1539-1650; O'Donnell, M. J. (Ed), Tetrahedron Symposia in Print: "α-Amino Acid Synthesis", 1988, 44, 5254-5614
3. Sammnen, J. "Bioactive Polymer Systems "Plenum Press, 1985, Chapter 12, 133-151.
4. For example see: Young, D. W. Tetrahedron Lett., 1994, 7277-7280; Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett., 1993, 381-384; Andres, C. J.; MacDonald, T. L.; Ocain, T. D.; Longhi, D. J. Org. Chem., 1993, 59, 6609-6613 and references cited therein.
5. For example see: Young, D. W. Tetrahedron Lett., 1994, 7277-7280; Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett., 1993, 381-384; Andres, C. J.; MacDonald, T. L.; Ocain, T. D.; Longhi, D. J. Org. Chem., 1993, 59, 6609-6613 and references cited therein.
6. For example see: Young, D. W. Tetrahedron Lett., 1994, 7277-7280; Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett., 1993, 381-384; Andres, C. J.; MacDonald, T. L.; Ocain, T. D.; Longhi, D. J. Org. Chem., 1993, 59, 6609-6613 and references cited therein.
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12. For syntheses of racemic α-phenylproline see: Smissman, E. E.; Chien, P. L.; Robinson, R. A. J. Org. Chem., 1970, 35, 3818-3820; Yasuo, H.; Suzuki, M.; Yoneda, N. Chem. Pharm. Bull., 1979, 27, 1931-1934.
13. For syntheses of racemic α-phenylproline see: Smissman, E. E.; Chien, P. L.; Robinson, R. A. J. Org. Chem., 1970, 35, 3818-3820; Yasuo, H.; Suzuki, M.; Yoneda, N. Chem. Pharm. Bull., 1979, 27, 1931-1934.
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21. 3. The mixture was filtered and the solvent removed in vacuo, then purified by silica gel (gradient elution petroleum ether / ethyl acetate = 8:2 to 6:4) to furnish the cyclised material. General procedure for reduction of lactams. To a solution of starting material (7) (321 mg, 1 mmol) in THF (15 mL) under a nitrogen atmosphere, was added a solution of 1.0 M diborane in THF (3mL) dropwise over 10 minutes. The temperature was maintained at approximately 0°C during the addition and the solution was then refluxed for 90 minutes. The flask was allowed to cool to room temperature. 1N HCl (4mL) was added and the solvent removed in vacuo. Subsequently a solution of 1 M NaOH was added until the mixture reached pH 12. The mixture was extracted with ether (3 × 20 mL), the combined extracts dried over MgSO4, and the solvent removed in vacuo. The crude residue was purified by chromatography on silica (eluent petroleum ether / ethyl acetate = 1/9) to afford the pure reduced material. General procedure for hydrogenolytic-degradation of the morpholinone template. The starting material (0.33 mmol) was dissolved in MeOH (40 mL). Palladium hydroxide on carbon (50 mg) and TFA (60μL) were added and the mixture was stirred under a hydrogen atmosphere (4 atm) at room temperature overnight. The catalyst was removed by filtration through Celite and the solvent removed in vacuo to afford the product.
22. 3): δ = 2.26 (m, 2H), 3.22 (m, 2H) 4.15 (dd, J = 7.1 Hz, 11.2 Hz, 1H), 4.39 (d, J = 4.2 Hz, 2H), 4.61
23. a radiation ω-2θ scans. The structures were solved by direct methods and refined by least squares using the CRYSTAL package. Atomic co-ordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.
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30. (e) Boa, A. N.; Guest, A. L.; Jenkins, P. R.; Fawcett, J.; Russell, D. R; Watson, D. J. Chem. Soc., Perkin Trans. 1, 1993, 477-481. For an application of enolate technology to Michael additions see: Schuerman, M. A.; Keverline, K. I.; Hiskey, R. G. Tetrahedron Lett., 1995, 825-828.