Enantioselective syntheses of α-, β-, and γ-aryl amino acids and esters

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1574-1575

  Park, Yong Sun ^a   Beak, Peter ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; ENANTIOMER; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030935907     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9700080     Document Type: Article

References (26)

1. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
2. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
3. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
4. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
5. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
6. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
7. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
8. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
9. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
10. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
11. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
12. Williams, R. M. Syntheses of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989. For recent reports see: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727. Davies, S. G.; Walters, A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488. Lipton, M.; Namdev, N. D.; Gigstad, K. M.; Iyer, M. S. J. Am. Chem. Soc. 1996, 118, 4910. Davis, F.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440. Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175. Cole, D. C. Tetrahedron 1994, 51, 9517. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222. Seki, M.; Matsumoto, K. Tetrahedron Lett. 1996, 37, 3165. North, M. Contemp. Org. Synth. 1996, 3, 323 and references cited therein.
13. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757.
14. The absolute configuration is assigned to (S)-3 on the basis of anomalous dispersions in the determination of the structure by X-ray crystallography. Caution: trimethyltin chloride is known to be toxic and should be used only with appropriate procedures. See: Sax, N. I.; Lewis, R. J. Dangerous Properties of Industrial Materials, 7th ed.; Van Nostrand Reinhold: New York, 1988; p 899.
15. The absolute configuration of (R)-18 was assigned by removal of the p-methoxyphenyl group with CAN and comparison to the optical rotation of authentic compound. Alcon, M.; Canas, M.; Poch, M.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 1995, 35, 1589.
16. The sequence of reduction, mesylation of the resulting alcohol, removal of the p-methoxyphenyl group with CAN, and cyclization with sodium hydride gave (S)-N-Boc 2-phenylpyrrolidine in 45% yield with an er of 90:10, establishing the absolute configuration of (S)-19. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715.
17. Still, W. C.; Sreekumar, C. J. Am. Chem. Soc. 1980, 102, 1201. Aggarwal, V. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 175.
18. Still, W. C.; Sreekumar, C. J. Am. Chem. Soc. 1980, 102, 1201. Aggarwal, V. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 175.
19. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552. We adopted the provisional assignment to give consistency with related reactions and note the present absolute configurations allow better assignments of retentive/invertive reactions than heretofore.
20. For other cases of invertive and retentive reactions of organolithium intermediates, see: Carstens, A.; Hoppe, D. Tetrahedron 1994, 50, 6097. Hoppe, D.; Carstens, A.; Kramer, T. Angew. Chem., Int. Ed. Engl. 1990, 29, 1424.
21. For other cases of invertive and retentive reactions of organolithium intermediates, see: Carstens, A.; Hoppe, D. Tetrahedron 1994, 50, 6097. Hoppe, D.; Carstens, A.; Kramer, T. Angew. Chem., Int. Ed. Engl. 1990, 29, 1424.
22. Derwing, C.; Hoppe, D. Synthesis 1996, 149.
23. Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763.
24. Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755.
25. Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. Weisenburger, J.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218.
26. Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. Weisenburger, J.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218.