[2,3]-Wittig rearrangement of enantiomerically enriched 3-substituted 1-propenyloxy-1-phenyl-2-propen-1-yl carbanions: Effect of heteroatoms and conjugating groups on planarization of an α-oxy-benzylcarbanion through a double bond

Chemistry - A European Journal

Volumn 15, Issue 18, 2009, Pages 4663-4666

  Sasaki, Michiko ^a   Ikemoto, Hidaka ^a   Kawahata, Masatoshi ^b   Yamaguchi, Kentaro ^b   Takeda, Kei ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Carbanions; Configuration analysis; Wittig reactions

Indexed keywords

CARBANIONS; CHIRALITY TRANSFERS; CONFIGURATION ANALYSIS; CONFIGURATIONAL STABILITIES; DOUBLE BONDS; ELECTRON-WITHDRAWING GROUPS; HETEROATOM SUBSTITUENTS; HETEROATOMS; INTRAMOLECULAR TRAPPING; PLANARIZATION; WITTIG REACTIONS; WITTIG REARRANGEMENTS;

CHEMICAL REACTIONS; STEREOCHEMISTRY;

IONS;

ANION; BUTYLLITHIUM; CARBON; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMISTRY; STEREOISOMERISM;

ANIONS; CARBON; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 65349151262     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802322     Document Type: Article

References (47)

1. a) The chemistry of organolithium compounds (Eds.: Z. Rappoport, I. Marek), Wiley, New York, 2004;
2. b) D. M. Hodgson, Organolithiums in enantionselective synthesis, Springer, New York, 2003;
3. c) J. Clayden, Organolithiums: Selectivity for synthesis, Pergamon, Oxford, 2002;
4. d) V. K. Aggarwal, Angew. Chem. 1994, 106, 185-187;
5. Angew. Chem. Int. Ed. Engl. 1994, 33, 175-177.
6. a) R. W. Hofmann, J. Lanz, R. Metternich, G. Tarara, D. Hoppe, Angew. Chem. 1987, 99, 1196;
7. Angew. Chem. Int. Ed. Engl. 1987, 26, 1145-1146;
8. b) R. Hirsch, R.W. Hoffmann, Chem. Bet: 1992, 125, 975-982;
9. c) R. W. Hoffmann, M. Julius, F. Chemla. T. Ruhland. G. Frenzen, Tetrahedron 1994, 50, 6049-6060;
10. d) A. Basu, D. Gallagher, P. Beak, J. Org. Chem. 1996, 61, 5718-5719. Also, see:
11. e) P. Beak, A. Basu, D. X. Gallagher, Y. S Park, S. Thayumanavan, Acc. Chem. Res. 1996, 29, 552-560.
12. M. Sasaki, M. Higashi, H. Masu, K. Yamaguchi, K. Takeda. Org. Lett. 2005, 7, 5913-5915.
13. For reviews on [2,3]-Wittig rearrangement, see: a) T. Nakai, K. Mikami, Chem. Rev. 1986, 86, 885-902;
14. b) J. A. Marshall in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991,pp. 975-1014;
15. c) K. Mikami, T. Nakai, Synthesis 1991,594-604;
16. d) T. Nakai, K. Mikami, Org. React. 1994, 46, 105-209;
17. e) T. Nakai, K. Tomooka, Pure Appl. Chem. 1997, 69, 595-600.
18. f) D. M. Hodgson. Organolithiums in enantionselective synthesis, Springer, New York, 2003, pp. 217-250.
19. K. Brickmann, R. Bruckner, Chem. Ber. 1993, 126, 1227-1239.
20. D. C Kapeller, L. Brecker, F. Hammerschmidt, Chem. Eur. J. 2007, 13, 9582-9588.
21. [3] It has been reported that [2,3]-Wittig rearrangement of lithiated allyl ethers and lithiated diallyl ethers proceeds with inversion of configuration at the lithium-bearing carbon atom. a) E. J. Verner, T. Cohen, J. Am. Chem. Soc. 1992, 114, 375-377;
22. b) R. Hoffmann, R. Brückner, Angew. Chem. 1992, 104, 646-648;
23. Angew. Chem. Int. Ed. Engl. 1992, 31, 647-649;
24. c) K. Tomooka, T. Igarashi, M. Watanabe, T. Nakai, Tetrahedron Lett. 1992, 33, 5795-5798.
25. P. R. Carlier, W. S. Mungall, G. Sohröder, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 2978-2979.
26. H. C. Brown, J. Chandrasekharan, P. V. Ramachandran, J. Am. Chem. Soc. 1988, 110, 1539-1546.
27. M. Sasaki, E. Kawanishi, Y. Shirakawa, M. Kawahata, H. Masu, K. Yamaguchi, K. Takeda, Eur. J. Org. Chem. 2008,3061-3064.
28. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
29. Although the choice of the base was based on best conversion, almost the same amounts of hexanes originating from nBuLi solution was used in the reactions with both of the bases.
30. Since the relative configurations of 7a-g and 7'a-g could not be assigned except 7'b, that of which was determined by an X-ray analysis, the more polar isomer and the less polar isomer were referred to as 7 and 7', respectively, on the basis of the polarity in the MPLC.
31. a) H. M. Walborsky, J. M. Motes, J. Am. Chem. Soc. 1970, 92, 2445-2450;
32. b) H. M. Walborsky, A. A. Youssef, J. M. Motes, J. Am. Chem. Soc. 1962, 84, 2465-2466;
33. c) H. M. Walborsky, F. M. Hornyak, J. Am. Chem. Soc. 1955, 77, 6026-6029;
34. d) P. R. Carlier, Y. Zhang, Org. Lett. 2007, 9, 1319-1322.
35. e) P. R. Carlier, Chirality 2003, 15, 340-347.
36. a) S. E. Denmark, R. L. Dorow, J. Org. Chem. 1990, 55, 5926-5928;
37. b) P. O'Brien, H. R. Powell, P. R. Raithby, S. Warren, J. Chem. Soc. Perkin Trans. 1 1997,1031-1039.
38. a) G. Boche, Angew. Chem. 1989, 101, 286-306;
39. Angew. Chem. Int. Ed. Engl. 1989, 28, 277-297;
40. b) H.-J. Gais, J. Vollhardt, H. J. Lindner, Angew. Chem. 1986, 98, 916-917;
41. Angew. Chem. Int. Ed. Engl. 1986, 25, 939-941;
42. c) H.-J. Gais, G. Hellmann, J. Am. Chem. Soc. 1992, 114, 4439-4440.
43. R. W. Hoffmann, T. Rühl, J. Harbach. Liebigs Ann. Chem. 1992,725-730.
44. B. Boche, A. Opel, M. Marsch, K. Harms. F. Hallera, J. C. W Lohrenz, C. Thümmler, W. Koch. Chem. Ber. 1992, 125, 2265-2273.
45. a) F. G. Bordwell, Acc. Chem. Res. 1998, 31, 456-463;
46. b) R. W. Taft, F. G. Bordwell. Acc. Chem. Res. 1998, 31, 463-469;
47. c) S. Zhang, X.-M. Zhang, F. G. Bordwell, J. Am. Chem. Soc. 1995, 117, 602-606.