Palladium-catalyzed stereospecific substitution of α,β- unsaturated γ,δ-epoxy esters by alcohols with double inversion of configuration: Synthesis of 4-alkoxy-5-hydroxy-2-pentenoates

Angewandte Chemie - International Edition

Volumn 47, Issue 4, 2008, Pages 750-754

  Yu, Xiao Qiang ^a   Yoshimura, Fumihiko ^a   Ito, Fumito ^a   Sasaki, Minoru ^a   Hirai, Atsushi ^a   Tanino, Keiji ^a   Miyashita, Masaaki ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KOGAKUIN UNIVERSITY   (Japan)

Author keywords

Alcohols; Esters; Homogeneous catalysis; Palladium; Synthetic methods

Indexed keywords

CATALYST ACTIVITY; EPOXY RESINS; ESTERS; PALLADIUM;

EPOXY ESTERS; HOMOGENEOUS CATALYSIS; STEREOSPECIFIC SUBSTITUTION; SYNTHETIC METHODS;

ALCOHOLS;

ALCOHOL DERIVATIVE; ALKANONE; EPOXIDE; ESTER; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; CATALYSIS; EPOXY COMPOUNDS; ESTERS; MOLECULAR CONFORMATION; PALLADIUM; PENTANONES; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM;

EID: 38349044274     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703889     Document Type: Article

References (23)

1. a) J. M. Klunder, G. H. Posner in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, chap. 1.5, pp. 207-239;
2. b) D. W. Knight in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, chap. 1.6, pp. 241-270;
3. c) P. J. Garratt in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, chap. 1.7, pp. 271-292;
4. d) G. H. Posner, Org. React. 1975, 22, 253;
5. e) R. M. Hanson, Chem. Rev. 1991, 91, 437;
6. f) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135;
7. g) C. Bonini, G. Righi, Synthesis 1994, 225.
8. For the substitution reactions of epoxy sulfides with double inversion of configuration, see a) C. Liu, Y. Hashimoto, K. Kudo, K. Saigo, Bull. Chem. Soc. Jpn. 1996, 69, 2095;
9. b) H. Hayakawa, N. Okada, M. Miyashita, Tetrahedron Lett. 1999, 40, 3191;
10. c) M. Sasaki, K. Tanino, M. Miyazawa, M. Miyashita, Tetrahedron Lett. 1999, 40, 9267;
11. d) M. Sasaki, K. Tanino, M. Miyashita, J. Org. Chem. 2001, 66, 5388;
12. e) A. Hirai, T. Tonooka, K. Wakatsuki, T. Tanino, M. Miyashita, Angew. Chem. 2002, 114, 847;
13. Angew. Chem. Int. Ed. 2002, 41, 819.
14. For other substitution reactions of epoxides with double inversion of configuration, see a) C. Liu, Y. Hashimoto, K. Saigo, Tetrahedron Lett. 1996, 37, 6177;
15. b) M. Sasaki, M. Hatta, K. Tanino, M. Miyashita, Tetrahedron Lett. 2004, 45, 1911.
16. M. Miyashita, T. Mizutani, G. Tadano, Y. Iwata, M. Miyazawa, K. Tanino, Angew. Chem. 2005, 117, 5224;
17. Angew. Chem. Int. Ed. 2005, 44, 5094.
18. A. Hirai, X.-Q. Yu, T. Tonooka, M. Miyashita, Chem. Commun. 2003, 2482.
19. X.-Q. Yu, A. Hirai, M. Miyashita, Chem. Lett. 2004, 33, 764.
20. N2 process has recently been reported, see J. Kjellgren, J. Aydin, O. A. Wallner, I. V. Saltanova, K. J. Szabó, Chem. Eur. J. 2005, 11, 5260.
21. B. M. Trost, E. J. McEachern, F. D. Toste, J. Am. Chem. Soc. 1998, 120, 12702.
22. 1H NMR analyses. (Chemical Equation Presented)
23. 3 was prepared by heating the commercially available reagent in an oven at 100°C for 3 h in vacuo prior to use.