Retention of regiochemistry of monosubstituted allyl acetates in the ruthenium catalysed allylic alkylation with malonate anion

Chemical Communications

Volumn , Issue 41, 2007, Pages 4283-4285

  Kawatsura, Motoi ^a   Ata, Fumio ^a   Hayase, Shuichi ^a   Itoh, Toshiyuki ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL ACETATE DERIVATIVE; MALONIC ACID; PALLADIUM; PHOSPHINE; RUTHENIUM; TOLUENE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; SUBSTITUTION REACTION;

EID: 35349001332     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b709218k     Document Type: Article

References (51)

1. J. Tsuji, Palladium Reagents and Catalysts: New Perspectives for the 21st Century, John Wiley & Sons, Chichester, 2004
2. B. M. Trost M. L. Crawley Chem. Rev. 2003 103 2921 2943
3. J. Tsuji, Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis, Wiley & Sons, Chichester, 2000
4. B. M. Trost and C. B. Lee, in Catalytic Asymmetric Synthesis II, ed., I. Ojima,, VCH, Weinheim, 2000
5. M. Johannsen K. A. Jørgensen Chem. Rev. 1998 98 1689 1708
6. A. Pfaltz and M. Lautens, in Comprehensive Asymmetric Catalysis I-III, ed., E. N. Jacobsen,,, A. Pfaltz, and, H. Yamamoto,, Springer-Verlag, Berlin, 1999
7. B. M. Trost D. L. Van Vranken Chem. Rev. 1996 96 395 422
8. T. Hayashi, in Catalytic Asymmetric Synthesis, ed., I. Ojima,, Wiley-VCH, Weinheim, 1993
9. T. Kondo and T. Mitsudo, in Ruthenium in Organic Synthesis, ed., S.-I. Murahashi,, Wiley-VCH, Weinheim, 2004
10. C. Bruneau J.-L. Renaud B. Demerseman Chem. Eur. J. 2006 12 5178 5187
11. T. Kondo H. Ono N. Satake T. Mitsudo Y. Watanabe Organometallics 1995 14 1945 1953
12. S.-W. Zhang T. Mitsudo T. Kondo Y. Watanabe J. Organomet. Chem. 1995 485 55 62
13. S.-W. Zhang T. Mitsudo T. Kondo Y. Watanabe J. Organomet. Chem. 1993 450 197 207
14. B. M. Trost P. L. Fraisse Z. T. Ball Angew. Chem., Int. Ed. 2002 41 1059 1061
15. N. Gürbüz I. Özdemir B. Cetinkaya J.-L. Renaud B. Demerseman C. Bruneau Tetrahedron Lett. 2006 47 535 538
16. M. D. Mbaye B. Demerseman J.-L. Renaud C. Bruneau J. Organomet. Chem. 2005 690 2149 2158
17. M. D. Mbaye B. Demerseman J.-L. Renaud L. Toupet C. Bruneau Adv. Synth. Catal. 2004 346 835 841
18. M. D. Mbaye B. Demerseman J.-L. Renaud L. Toupet C. Bruneau Angew. Chem., Int. Ed. 2003 42 5066 5068
19. J.-L. Renaud C. Bruneau B. Demerseman Synlett 2003 408 410
20. R. Hermatschweiler I. Fernández F. Breher P. S. Pregosin L. F. Veiros M. Calhorda Angew. Chem., Int. Ed. 2005 44 4397 4400
21. R. Hermatschweiler I. Fernández P. S. Pregosin E. J. Watson A. Albinati S. Rizzato L. F. Veiros M. J. Calhorda Organometallics 2005 24 1809 1812
22. I. Fernández R. Hermatschweiler P. S. Pregosin A. Albinati S. Rizzato Organometallics 2006 25 323 330
23. R. Hermatschweiler I. Fernández P. S. Pregosin F. Breher Organometallics 2006 25 1440 1441
24. M. Kawatsura F. Ata S. Wada S. Hayase H. Uno T. Itoh Chem. Commun. 2007 298 300
25. J. C. Fiaud J. L. Malleron Tetrahedron Lett. 1981 22 1399 1402
26. B. M. Trost R. C. Bunt J. Am. Chem. Soc. 1996 118 235 236
27. T. Hayashi M. Kawatsura Y. Uozumi Chem. Commun. 1997 561 562
28. T. Hayashi M. Kawatsura Y. Uozumi J. Am. Chem. Soc. 1998 120 1681 1687
29. G. C. Lloyd-Jones S. C. Stephen Chem. Commun. 1998 2321 2322
30. G. C. Lloyd-Jones S. C. Stephen Chem. Eur. J. 1998 4 2539 2549
31. C. P. Butts J. Crosby G. C. Lloyd-Jones S. C. Stephen Chem. Commun. 1999 1707 1708
32. P. Kocovsky S. Vyskocil I. Cisarova J. Sejbal I. Tislerova M. Smrcina G. C. Lloyd-Jones S. C. Stephen C. P. Butts M. Murray V. Langer J. Am. Chem. Soc. 1999 121 7714 7715
33. G. C. Lloyd-Jones S. C. Stephen M. Murray C. P. Butts S. Vyskocil P. Kocovsky Chem. Eur. J. 2000 6 4348 4357
34. I. J. S. Fairlamb G. C. Lloyd-Jones S. Vyskocil P. Kocovsky Chem. Eur. J. 2002 8 4443 4453
35. L. Gouriou G. C. Lloyd-Jones S. Vyskocil P. Kocovsky J. Organomet. Chem. 2003 687 525 537
36. S. Vyskocil M. Smrcina V. Hanus M. Polasek P. Kocovsky J. Org. Chem. 1998 63 7738 7748
37. B. J. Lussem H.-J. Gais J. Org. Chem. 2004 69 4041 4052
38. J. W. Faller N. Sarantopoulos Organometallics 2004 23 2179 2185
39. P. Fristrup T. Jensen J. Hoppe P.-O. Norrby Chem. Eur. J. 2006 12 5352 5360
40. P. A. Evans J. D. Nelson J. Am. Chem. Soc. 1998 120 5581 5582
41. R. Takeuchi N. Kitamura New J. Chem. 1998 22 659 660
42. B. L. Ashfeld K. A. Miller S. F. Martin Org. Lett. 2004 6 1321 1324
43. D. L. Hughes M. Palucki N. Yasuda R. A. Reamer P. J. Reider J. Org. Chem. 2002 67 2762 2768
44. J. Lehmann G. C. Lloyd-Jones Tetrahedron 1995 51 8863 8874
45. G. C. Lloyd-Jones A. Pfaltz Angew. Chem., Int. Ed. Engl. 1995 34 462 464
46. B. Plietker Angew. Chem., Int. Ed. 2006 45 1469 1473
47. We also examined the reaction by KHMDS and NaH, but they resulted in a <90% branch selectivity
48. 3 also proceeded with an 80% linear selectivity, but the linear type product was a mixture of the E and Z stereoisomers (E/Z = 90/10)
49. The linear selectivities with LiHMDS in toluene and NaHMDS in THF were 77% (89% yield) and 82% (85% yield), respectively
50. H. Le Bozec D. Touchard P. H. Dixneuf Adv. Organomet. Chem. 1989 29 163 247
51. B. Demerseman M. D. Mbaye D. Semeril L. Toupet C. Bruneau P. H. Dixneuf Eur. J. Inorg. Chem. 2006 1174 1181