Catalyzed Olefin Isomerization Leading to Highly Stereoselective Claisen Rearrangements of Aliphatic Allyl Vinyl Ethers

Journal of the American Chemical Society

Volumn 125, Issue 43, 2003, Pages 13000-13001

  Nelson, Scott G ^a   Bungard, Christopher J ^a   Wang, Kan ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALLYL VINYL ETHER; ALIPHATIC COMPOUND; ALKENE; ETHER DERIVATIVE; IRIDIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; ISOMERISM; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

ALDEHYDES; ALKENES; ALLYL COMPOUNDS; CATALYSIS; IRIDIUM; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 0142214632     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037655v     Document Type: Article

References (29)

1. (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423.
2. (b) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43.
3. (c) Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 1461.
4. (d) Nubbemeyer, U. Synthesis 2003, 961.
5. (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 827.
6. (b) Wilson, S. R. Org. React. (New York) 1993, 43, 93.
7. (c) Paquette, L. A. Tetrahedron 1997, 53, 13971.
8. For extensive development of aliphatic Claisen rearrangements, see: Nonoshita, K.; Maruoka, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 541 and references therein.
9. For alternative vinyl ether preparations in Claisen rearrangements, see: (a) Mikami, K.; Takahashi, K.; Nakai, T. Tetrahedron Lett. 1987, 28, 5879.
10. (b) Sugiura, M.; Yanagisawa, M.; Nakai, T. Synlett 1995, 447.
11. (c) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 2000, 122, 3785.
12. (d) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426.
13. (e) Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978.
14. For the use of functionalized allyl vinyl ether substrates derived from α-dicarbonyl substrates in asymmetric Claisen rearrangements, see: (a) Abraham, L.; Czerwonka, R.; Hiersemann, M. Angew. Chem., Int. Ed. 2001, 40, 4700.
15. See also: (b) ref 4c.
16. (a) Ni(0) catalysts: Wille, A.; Tomm, S.; Frauenrath, H. Synthesis 1998, 305.
17. (b) Ir(1) catalysts: Higashino, T.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2000, 2, 4193.
18. (c) Reuter, J. M.; Salomon, R. G. J. Org. Chem. 1977, 42, 3360.
19. (d) Ru(II) catalysts: Ben Ammar, H.; Le Nôtre, J.; Salem, M.; Kaddachi, M. T.; Dixneuf, P. H. J. Organomet. Chem. 2002, 662, 63.
20. For a detailed investigation of Ir(I)-catalyzed allylic ether isomerization, see: Ohmura, T.; Yamamoto, Y.; Miyaura, N. Organometallics 1999, 18, 413 and references therein.
21. Onderdelinden, A. L.; van der Ent, A. Inorg. Chim. Acta 1972, 6, 420.
22. 2 employing various methods for reductive removal of the diene ligand uniformly provided Ir(I)-phosphine catalysts exhibiting inferior activity relative to analogous complexes prepared from dimer 3.
23. 4. Miyaura has also found acetone to accelerate related catalyzed isomerizations; see ref 7.
24. Complex 5a is formulated as the tris(phosphine) complex on the basis of reaction stoichiometry and is not necessarily intended to represent the reactive catalyst complex that may be accessed by reversible phosphine dissociation.
25. 2-AIH reduction of the initial Claisen products due to epimerization of the α-chiral aldehydes during attempted chromatographic purification. See Supporting Information for full procedural details.
26. Wilson, S. R.; Price, M. F. J. Am. Chem. Soc. 1982, 104, 1124.
27. A similar observation was made in Claisen rearrangements involving substrates prepared by Hg(II)-mediated ether exchange. See ref 3.
28. Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
29. 2Zn addition was not optimized.