Synthesis of silicon containing alanines

Tetrahedron

Volumn 54, Issue 25, 1998, Pages 7221-7228

  Sibi, Mukund P ^a   Harris, Brant J ^a   Shay, John J ^a   Hajra, Saumen ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

Oxazolidinone; Silicon Amino Acids; Silyl Copper Reagents

Indexed keywords

ALANINE; SILICON;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032543531     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00356-1     Document Type: Article

References (35)

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6. 2. A variety of diphenyl alanines have been synthesized by a novel methodology. Sibi, M. P.; Deshpande, P. K.; La Loggia, A. J. US Patent 5623087.
7. 3. There are few reports on the synthesis of silicon containing amino acids: Walkup, R. D.; Cole, D. C.; Whittlesey, B. R. J. Org. Chem. 1995, 60, 2630 and references cited therein. Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277. Smith, R. J.; Bratovanov, S.; Bienz, S. Tetrahedron 1997, 53, 13695.
8. 3. There are few reports on the synthesis of silicon containing amino acids: Walkup, R. D.; Cole, D. C.; Whittlesey, B. R. J. Org. Chem. 1995, 60, 2630 and references cited therein. Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277. Smith, R. J.; Bratovanov, S.; Bienz, S. Tetrahedron 1997, 53, 13695.
9. 3. There are few reports on the synthesis of silicon containing amino acids: Walkup, R. D.; Cole, D. C.; Whittlesey, B. R. J. Org. Chem. 1995, 60, 2630 and references cited therein. Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277. Smith, R. J.; Bratovanov, S.; Bienz, S. Tetrahedron 1997, 53, 13695.
10. 4. (a) Sibi, M. P.; Renhowe, P. Tetrahedron Lett. 1990, 31, 7407.
11. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115.
12. (c) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. J. Org. Chem. 1992, 57, 4329.
13. 5. Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans 1, 1994, 1675.
14. 6. Procedure for the synthesis (R)-4-hydroxymethyl-2-oxazolidinone, precursor for 1, has been communicated. Sibi, M. P.; Harris, B.; Renhowe, P. A.; Christensen, J. W.; Rutherford, D.; Li, B.; Lu, J. Org. Synth. submitted for publication. Also see ref. 4 for some details.
15. 7. For general information on organocopper reagents see: Organocopper Reagents, Taylor, R. J. K. Ed.: Oxford University Press, Oxford, 1994; Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992. For recent reviews on organocopper reagents see: Krause, N.; Gerold, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 186; Lipshutz, B.; Sengupta, S. Org. React. 1992, 41, 135; Lipshutz, B. in Organometallics in Synthesis, Schlosser, M. Ed.: Wiley, Chichester, 1994.
16. 7. For general information on organocopper reagents see: Organocopper Reagents, Taylor, R. J. K. Ed.: Oxford University Press, Oxford, 1994; Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992. For recent reviews on organocopper reagents see: Krause, N.; Gerold, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 186; Lipshutz, B.; Sengupta, S. Org. React. 1992, 41, 135; Lipshutz, B. in Organometallics in Synthesis, Schlosser, M. Ed.: Wiley, Chichester, 1994.
17. 7. For general information on organocopper reagents see: Organocopper Reagents, Taylor, R. J. K. Ed.: Oxford University Press, Oxford, 1994; Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992. For recent reviews on organocopper reagents see: Krause, N.; Gerold, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 186; Lipshutz, B.; Sengupta, S. Org. React. 1992, 41, 135; Lipshutz, B. in Organometallics in Synthesis, Schlosser, M. Ed.: Wiley, Chichester, 1994.
18. 7. For general information on organocopper reagents see: Organocopper Reagents, Taylor, R. J. K. Ed.: Oxford University Press, Oxford, 1994; Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992. For recent reviews on organocopper reagents see: Krause, N.; Gerold, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 186; Lipshutz, B.; Sengupta, S. Org. React. 1992, 41, 135; Lipshutz, B. in Organometallics in Synthesis, Schlosser, M. Ed.: Wiley, Chichester, 1994.
19. 7. For general information on organocopper reagents see: Organocopper Reagents, Taylor, R. J. K. Ed.: Oxford University Press, Oxford, 1994; Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992. For recent reviews on organocopper reagents see: Krause, N.; Gerold, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 186; Lipshutz, B.; Sengupta, S. Org. React. 1992, 41, 135; Lipshutz, B. in Organometallics in Synthesis, Schlosser, M. Ed.: Wiley, Chichester, 1994.
20. 8. The silyl lithiums were generated form the corresponding chlorosilanes and lithium metal under sonication conditions: Sharma, S.; Oehlschlager, A. C. Tetrahedron 1989, 45, 557. For the preparation and use of silyl copper reagents see Crump, R. A. N. C.; Fleming, I.; Hill, J. H. M.; Parker, D.; Reddy, L.; Waterson, D. J. Chem. Soc., Perkin Trans. 1 1992, 3277 and references cited therein; Cuadrado, P.; González, A. M.; González, B.; Pulido, F. J. Synth. Commun. 1989, 19, 275; Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076.
21. 8. The silyl lithiums were generated form the corresponding chlorosilanes and lithium metal under sonication conditions: Sharma, S.; Oehlschlager, A. C. Tetrahedron 1989, 45, 557. For the preparation and use of silyl copper reagents see Crump, R. A. N. C.; Fleming, I.; Hill, J. H. M.; Parker, D.; Reddy, L.; Waterson, D. J. Chem. Soc., Perkin Trans. 1 1992, 3277 and references cited therein; Cuadrado, P.; González, A. M.; González, B.; Pulido, F. J. Synth. Commun. 1989, 19, 275; Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076.
22. 8. The silyl lithiums were generated form the corresponding chlorosilanes and lithium metal under sonication conditions: Sharma, S.; Oehlschlager, A. C. Tetrahedron 1989, 45, 557. For the preparation and use of silyl copper reagents see Crump, R. A. N. C.; Fleming, I.; Hill, J. H. M.; Parker, D.; Reddy, L.; Waterson, D. J. Chem. Soc., Perkin Trans. 1 1992, 3277 and references cited therein; Cuadrado, P.; González, A. M.; González, B.; Pulido, F. J. Synth. Commun. 1989, 19, 275; Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076.
23. 8. The silyl lithiums were generated form the corresponding chlorosilanes and lithium metal under sonication conditions: Sharma, S.; Oehlschlager, A. C. Tetrahedron 1989, 45, 557. For the preparation and use of silyl copper reagents see Crump, R. A. N. C.; Fleming, I.; Hill, J. H. M.; Parker, D.; Reddy, L.; Waterson, D. J. Chem. Soc., Perkin Trans. 1 1992, 3277 and references cited therein; Cuadrado, P.; González, A. M.; González, B.; Pulido, F. J. Synth. Commun. 1989, 19, 275; Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076.
24. 9. The molarity of the silyl lithiums were determined by titration. Fleming, I.; Roberts, R. S.; Smith, S. C. Tetrahedron Lett. 1996, 37, 9395.
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26. 11. Typically, 1-7% of an allyl carbamate was formed by cleavage of the oxazolidinone in reactions where the displacements were not efficient.
27. 12. The utility of silyl oxazolidinones 2 in conjugate additions, aldol condensations and Diels-Alder reactions are currently being explored.
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34. (f) Sibi, M. P.; Deshpande, P. K.; La Loggia, A. J.; Christensen, J. W. Tetrahedron Lett. 1995, 56, 8961.
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