Asymmetric alkylation of dimethoxyphosphoryl-N-[1-(S)-α-methyl- benzyl]acetamide enolates. Synthesis of both stereoisomers from the same source of chirality by changing the equivalents of LDA

Chemical Communications

Volumn , Issue 10, 2005, Pages 1336-1338

  Ordóñez, Mario ^a   Hernández Fernández, Eugenio ^a   Xahuentitla, Janet ^a   Cativiela, Carlos ^b  

^a CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^b CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; DIMETHOXYPHOSPHORYL N (1 ALPHA METHYLBENZYL)ACETAMIDE ENOLATE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; METHODOLOGY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 16244412973     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b416616g     Document Type: Article

References (27)

1. R. K. Boeckman, Jr., D. J. Boehmler and R. A. Musselman, Org. Lett., 2001, 3, 3777.
2. C. Alvarez-Ibarra, A. G. Csaky, R. Maroto and M. L. Quiroga, J. Org. Chem., 1995, 60, 7934.
3. A. G. Myers and L. McKinstry, J. Org. Chem., 1996, 61, 2428.
4. J. H. Smitrovich, L. DiMichele, C. Qu, G. N. Boice, T. D. Nelson, M. A. Huffman and J. Murry, J. Org. Chem., 2004, 69, 1903; K. Ando, Y. Takemasa, K. Tomioka and K. Koga, Tetrahedron, 1993, 49, 1579 and references cited therein.
5. J. H. Smitrovich, L. DiMichele, C. Qu, G. N. Boice, T. D. Nelson, M. A. Huffman and J. Murry, J. Org. Chem., 2004, 69, 1903; K. Ando, Y. Takemasa, K. Tomioka and K. Koga, Tetrahedron, 1993, 49, 1579 and references cited therein.
6. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, ed. V. P. Kukhar and H. R. Hudson, John Wiley, New York, 2000, and references cited therein.
7. F. A. Davis, S. Lee, H. Yan and D. D. Titus, Org. Lett., 2001, 3, 1757; R. Kuwano, R. Nishio and Y. Ito, Org. Lett., 1999, 1, 837.
8. F. A. Davis, S. Lee, H. Yan and D. D. Titus, Org. Lett., 2001, 3, 1757; R. Kuwano, R. Nishio and Y. Ito, Org. Lett., 1999, 1, 837.
9. M. Ordóñez, A. González-Morales, C. Ruiz, R. De la Cruz-Cordero and M. Fernández-Zertuche, Tetrahedron: Asymmetry, 2003, 14, 1775; M. Ordóñez, A. González-Morales and H. Salazar-Fernández, Tetrahedron: Asymmetry, 2004, 15, 2719.
10. M. Ordóñez, A. González-Morales, C. Ruiz, R. De la Cruz-Cordero and M. Fernández-Zertuche, Tetrahedron: Asymmetry, 2003, 14, 1775; M. Ordóñez, A. González-Morales and H. Salazar-Fernández, Tetrahedron: Asymmetry, 2004, 15, 2719.
11. Alkylation of amides bearing (S)-α-methylbenzylamine has been reported by V. M. Gutiérrez-García, H. López-Ruíz, G. Reyes-Rangel and E. Juaristi, Tetrahedron, 2001, 57, 6487.
12. B. A. Arbuzov, Pure Appl. Chem., 1964, 9, 307.
13. C. P. Schickli and D. Seebach, Liebigs. Ann. Chem., 1991, 655; S. Y. Lee, C.-W. Lee and D. Y. Oh, J. Org. Chem., 1999, 64, 7017.
14. C. P. Schickli and D. Seebach, Liebigs. Ann. Chem., 1991, 655; S. Y. Lee, C.-W. Lee and D. Y. Oh, J. Org. Chem., 1999, 64, 7017.
15. U. Schöllkopf, H.-H. Hausberg, M. Segal, U. Reiter, I. Hoppe, W. Saenger and K. Lindner, Liebigs Ann. Chem., 1981, 439; U. Schöllkopf, H. H. Hausberg, I. Hoppe, M. Segal and U. Reiter, Angew. Chem., Int. Ed. Engl., 1978, 17, 117.
16. U. Schöllkopf, H.-H. Hausberg, M. Segal, U. Reiter, I. Hoppe, W. Saenger and K. Lindner, Liebigs Ann. Chem., 1981, 439; U. Schöllkopf, H. H. Hausberg, I. Hoppe, M. Segal and U. Reiter, Angew. Chem., Int. Ed. Engl., 1978, 17, 117.
17. S. Liao and D. B. Collum, J. Am. Chem. Soc., 2003, 125, 15114; Y.-J. Kim and A. Streitwieser, Org. Lett., 2002, 4, 573; X. Sun and D. B. Collum, J. Am. Chem. Soc., 2000, 122, 2459.
18. S. Liao and D. B. Collum, J. Am. Chem. Soc., 2003, 125, 15114; Y.-J. Kim and A. Streitwieser, Org. Lett., 2002, 4, 573; X. Sun and D. B. Collum, J. Am. Chem. Soc., 2000, 122, 2459.
19. S. Liao and D. B. Collum, J. Am. Chem. Soc., 2003, 125, 15114; Y.-J. Kim and A. Streitwieser, Org. Lett., 2002, 4, 573; X. Sun and D. B. Collum, J. Am. Chem. Soc., 2000, 122, 2459.
20. M. Drag, R. Latajka, E. Gumienná-Kontecka, H. Kozlowski and P. Kafarski, Tetrahedron: Asymmetry, 2003, 14, 1837; A. E. Wróblewski and D. G. Piotrowska, Tetrahedron: Asymmetry, 2002, 13, 2509; T. Yamagishi, K. Suemune, T. Yokomatsu and S. Shibuya, Tetrahedron Lett., 2001, 42, 5033; F. Hammerschmidt, W. Lindner, F. Wuggenig and E. Zarbl, Tetrahedron: Asymmetry, 2000, 11, 2955.
21. M. Drag, R. Latajka, E. Gumienná-Kontecka, H. Kozlowski and P. Kafarski, Tetrahedron: Asymmetry, 2003, 14, 1837; A. E. Wróblewski and D. G. Piotrowska, Tetrahedron: Asymmetry, 2002, 13, 2509; T. Yamagishi, K. Suemune, T. Yokomatsu and S. Shibuya, Tetrahedron Lett., 2001, 42, 5033; F. Hammerschmidt, W. Lindner, F. Wuggenig and E. Zarbl, Tetrahedron: Asymmetry, 2000, 11, 2955.
22. M. Drag, R. Latajka, E. Gumienná-Kontecka, H. Kozlowski and P. Kafarski, Tetrahedron: Asymmetry, 2003, 14, 1837; A. E. Wróblewski and D. G. Piotrowska, Tetrahedron: Asymmetry, 2002, 13, 2509; T. Yamagishi, K. Suemune, T. Yokomatsu and S. Shibuya, Tetrahedron Lett., 2001, 42, 5033; F. Hammerschmidt, W. Lindner, F. Wuggenig and E. Zarbl, Tetrahedron: Asymmetry, 2000, 11, 2955.
23. M. Drag, R. Latajka, E. Gumienná-Kontecka, H. Kozlowski and P. Kafarski, Tetrahedron: Asymmetry, 2003, 14, 1837; A. E. Wróblewski and D. G. Piotrowska, Tetrahedron: Asymmetry, 2002, 13, 2509; T. Yamagishi, K. Suemune, T. Yokomatsu and S. Shibuya, Tetrahedron Lett., 2001, 42, 5033; F. Hammerschmidt, W. Lindner, F. Wuggenig and E. Zarbl, Tetrahedron: Asymmetry, 2000, 11, 2955.
24. M. S. Rahman, M. Oliana and K. K. Hu, Tetrahedron: Asymmetry, 2004, 15, 1835; A. M. Maj, K. M. Pietrusiewics, I. Suisse, F. Agbossou and A. Mortreux, J. Organomet. Chem., 2001, 626, 157; A. M. Maj, K. M. Pietrusiewicz, I. Suisse, F. Agbossou and A. Mortreux, Tetrahedron: Asymmetry, 1999, 10, 831.
25. M. S. Rahman, M. Oliana and K. K. Hu, Tetrahedron: Asymmetry, 2004, 15, 1835; A. M. Maj, K. M. Pietrusiewics, I. Suisse, F. Agbossou and A. Mortreux, J. Organomet. Chem., 2001, 626, 157; A. M. Maj, K. M. Pietrusiewicz, I. Suisse, F. Agbossou and A. Mortreux, Tetrahedron: Asymmetry, 1999, 10, 831.
26. M. S. Rahman, M. Oliana and K. K. Hu, Tetrahedron: Asymmetry, 2004, 15, 1835; A. M. Maj, K. M. Pietrusiewics, I. Suisse, F. Agbossou and A. Mortreux, J. Organomet. Chem., 2001, 626, 157; A. M. Maj, K. M. Pietrusiewicz, I. Suisse, F. Agbossou and A. Mortreux, Tetrahedron: Asymmetry, 1999, 10, 831.
27. E. Juaristi, A. Martinez-Richa, A. Garcia-Rivera and J. S. Cruz-Sánchez, J. Org. Chem., 1983, 48, 2603.