Synthesis and derivatization of substituted (R)- and (S)-C-allylglycines

Advanced Synthesis and Catalysis

Volumn 346, Issue 11, 2004, Pages 1335-1354

  Zhang, Nong ^a   Münch, Winfried ^a   Nubbemeyer, Udo ^b  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Allylation; Aza Claisen rearrangement; C allylglycine; Chiral auxiliary; Ring closing metathesis

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYLGLYCINE; AZIDE; CYCLOHEXENE DERIVATIVE; LITHIUM DERIVATIVE; PROLINE;

ADDITION REACTION; ARTICLE; CATALYST; CHEMICAL REACTION; CLAISEN REARRANGEMENT; DERIVATIZATION; ENANTIOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 7044233368     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404102     Document Type: Article

References (113)

1. a) T. Fukami, T. Yamakawa, K. Niiyama, H. Kojima, Y. Amano, J. Med. Chem. 1996, 39, 2313-2330;
2. b) N. Kurokawa, Y. Ohfune, Y. Tetrahedron 1993, 49, 6195-6222;
3. c) Q. B. Broxterman, B. Kaptein, J. Kamphuis, H. E. Schoemaker, J. Org. Chem. 1992, 57, 6286-6294;
4. d) J. E. Baldwin, W. J. Norris, R. T. Freeman, M. Bradley, R. M. Adlington, J. Chem. Soc. Chem. Commun. 1988, 1128-1130;
5. e) U. Voigtmann, S. Blechert, S. Synthesis 2000, 893-898;
6. f) C. E. Grossmith, F. Senia, J. Wagner, Synlett 1999, 1660-1662;
7. g) Y. Gao, P. Lane-Bell, J. C. Vederas, J. Org. Chem. 1998, 63, 2133-2143;
8. h) F. P. J. T. Rutjes, H. E. Schoemaker, Tetrahedron Lett. 1997, 38, 677-680;
9. i) H. G. Bossler, D. Seebach, Helv. Chim. Acta 1994, 77, 1124-1165;
10. j) D. Seebach, A. K. Beck, H. G. Bossle, C. Gerber, S. Y. Ko, Helv. Chim. Acta 1993, 76, 1564-1590;
11. k) J. E. Baldwin, R. M. Adlington, S. L. Flitsch, H.-H. Ting, N. J. Turner, J. Chem. Soc. Chem. Commun. 1986, 1305-1308.
12. a) K. M. Depew, T. M. Kamenecka, S. J. Danishefsky, Tetrahedron Lett. 2000, 41, 289-292;
13. b) F. P. J. T. Rutjes, J. J. N. Veerman, W. J. N. Meester, H. Hiemstra, H. E. Schoemaker, Eur. J. Org. Chem. 1999, 1127-1136;
14. c) K. H. Ahn, S.-K. Kim, C. Ham, Tetrahedron Lett. 1998, 39, 6321-6322;
15. d) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. Int. Ed. 1998, 37, 2995-2998; Angew. Chem. 1998, 110, 3166-3168;
16. d) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. Int. Ed. 1998, 37, 2995-2998; Angew. Chem. 1998, 110, 3166-3168;
17. e) K. J. Hale, J. Cai, V. Delisser, S. Manaviazar, S. A. Peak, Tetrahedron 1996, 52, 1047-1068;
18. f) W. Oppolzer, O. Tamura, J. Deerberg, Helv. Chim. Acta 1992, 75, 1965-1978;
19. g) D. A. Evans, T. C. Britton, R. L. Dorow, J. F. Dellaria, Tetrahedron 1988, 44, 5525-5540;
20. h) O. Kitagawa, T. Hanano, N. Kikuchi, T. Taguchi, Tetrahedron Lett. 1993, 34, 2165-2168;
21. i) D. A. Evans, T. C. Britton, J. A. Ellman, R. L. Dorow, J. Am. Chem. Soc. 1990, 112, 4011-4030;
22. j) A. G. Myers, P. Schnider, S. Kwon, D. W. Kung, J. Org. Chem. 1999, 64, 3322-3327;
23. k) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519-6520;
24. l) E. Juaristi, J. L. Leon-Romo, Y. Ramirez-Quiros, J. Org. Chem. 1999, 64, 2914-2918;
25. m) G. Guillena, C. Najera, Tetrahedron: Asymmetry 1998, 9, 3935-3938;
26. n) S. D. Bull, S. G. Davies, S. W. Epstein, M. A. Leech, J. V. A. Ouzman, J. Chem. Soc. Perkin Trans. 1 1998, 2321-2330;
27. o) G. Porzi, S. Sandri, P. Verrocchio, Tetrahedron: Asymmetry 1998, 9, 119-132;
28. q) W. Oppolzer, H. Bienayme, A. Genevois-Borella, J. Am. Chem. Soc. 1991, 113, 9660-9661;
29. r) X. Fang, M. Johannsen, S. Yao, N. Gathergood, R. G. Hazell, K. A. Joergensen, J. Org. Chem. 1999, 64, 4844-4849;
30. s) Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, Heterocycles 1998, 47, 765-780;
31. t) G. Kardassis, P. Brungs, E. Steckhan, Tetrahedron 1998, 54, 3471-3478;
32. u) T.-P. Loh, D. S.-C. Ho, K.-C. Xu, K.-Y. Sim, Tetrahedron Lett. 1997, 38, 865-868;
33. v) S. Hanessian, R.-Y. Yang, Tetrahedron Lett. 1996, 37, 5273-5276 and 8997-9000;
34. w) N. Kurokawa, Y. Ohfune, Tetrahedron 1993, 49, 6195-6222;
35. x) Y. Yamamoto, W. Ito, Tetrahedron 1988, 44, 5415-5424;
36. y) U. Kazmaier, S. Maier, J. Org. Chem. 1999, 64, 4574-4575;
37. z) U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213-2214; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012-2014.
38. z) U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213-2214; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012-2014.
39. a) N. Zhang, U. Nubbemeyer, Synthesis 2002, 242-252;
40. b) S. Laabs, W. Münch, J.-W. Bats, U. Nubbemeyer, Tetrahedron 2002, 58, 1317-1334.
41. a) D. A. Evans, J. A. Ellman, R. L. Dorow, Tetrahedron Lett. 1987, 28, 1123-1126;
42. b) D. A. Evans, T. C. Britton, J. A. Ellman, R. L. Dorow, J. Am. Chem. Soc. 1990, 112, 4011-4030.
43. a) G. A. Molander, J. A. McKie, J. Org. Chem. 1993, 55, 7216-7227;
44. b) L.-A. Sandrine, M. Savignac, C. Dupuis, J. P. Genet, Bull. Soc. Chim. Fr. 1995, 132, 1157-1166.
45. J. Cossy, O. Mirguet, D. G. Pardo, Synlett 2001, 1575-1577.
46. a) S. J. Danishefsky, N. Mantlo, J. Am. Chem. Soc. 1988, 110, 8129-8133;
47. b) J-F. Nave, P. J. Casara, D. L. Taylor, A. S. Tyms, M. Kenny, S. Halazy, Bioorg. Med. Chem. Lett. 1996, 6, 179-184.
48. S. Lemarie-Audoire, M. Savignac, C. Dupuis, J. P. Genet, Bull. Soc. Chim. Fr. 1995, 132, 1157-1166.
49. E. J. Corey, A. Venkatesvarlu, J. Am. Chem. Soc. 1972, 94, 6190-191.
50. H. G. Aurich, G. Frenzen, C. Gentes, Christian; Chem. Ber. 1993, 126, 787-796.
51. E. Winterfeldt, Synthesis 1975, 617-630.
52. a) A. Padwa, J. E. Cochran, O. Kappe, J. Org. Chem. 1996, 61, 3706-3714;
53. b) J. Jin, S. M. Weinreb, J. Am. Chem. Soc. 1997, 119, 5773-5784;
54. c) H. Staudinger, J. Meyer, Helv. Chim. Acta. 1919, 2, 635-646.
55. a) S. Groß, S. Laabs, A. Scherrmann, A. Sudau, N. Zhang, U. Nubbemeyer, J. Prak. Chem. 2000, 342, 711-714;
56. b) L. A. Carpino, E.-S. M. E. Mansour, D. Sadat-Alaee, J. Org. Chem. 1991, 56, 2611-2614;
57. c) S. V. V. Babu, H. N. Gopi, K. Ananda, Ind. J. Chem. Sec. B 2000, 39, 384-386;
58. d) G. A. Olah, M. Nojima, I. Kerekes, Synthesis 1973, 487-488;
59. e) G. A. Olah, S. Kuhn, S. Beke, Chem. Ber. 1956, 89, 862-864.
60. a) J. von Braun, Ber. Dtsch. Chem. Ges. 1907, 40, 3914-3933;
61. b) J. H. Cooley, E. J. Evain, Synthesis 1989, 1-7.
62. [3] were characterized by the same chemical behaviour and analogous spectral data.
63. Most of the rearrangements furnishing C-allylglycine amides were characterized by the same epimerization behaviour improving the highly efficient auxiliary directed chiral induction. In several cases, the yield of the diastereomer was low because of competing reactions. However, the generation of a new second diastereomer could be always shown satisfactorily.
64. P. M. Rita, M. I. Calaza, F. J. Sardina, J. Org. Chem. 1997, 62, 6862-6869.
65. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
66. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
67. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
68. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
69. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
70. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
71. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
72. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
73. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
74. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
75. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
76. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
77. Reviews on Claisen rearrangements: a) R. K. Hill, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1984, Vol. 3, pp. 503-572; b) F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452; c) P. Wipf, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming, L. A. Paquette), Pergamon Press, New York, 1991, Vol. 5, pp. 827-873; d) H. Frauenrath, in: Houben Weyl, Stereoselective Synthesis, Vol. E21d, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York 1995, pp. 3301-3756; e) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43-50; f) S. M. Allin, R. D. Baird, Curr. Org. Chem. 2001, 395-415; g) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471; h) Y. Chai, S. P. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928; i) K. C. Majumdar, T. Bhattacharyya, Ind. J. Chem. 2002, 79, 112-121 ; for enantioselective Claisen rearrangements see: j) D. Enders, M. Knopp, R. Schiffers, Tetrahedron Asymmetry 1996, 7, 1847-1882; k) U. Nubbemeyer, Synthesis 2003, 961-1008; originally, ketene Claisen rearrangements have been described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: l) R. Malherbe, D. Bellus, Helv. Chim. Acta 1978, 61, 3096-3099; m) R. Malherbe, G. Rist, D. Bellus, J. Org. Chem. 1983, 48, 860-869.
78. a) D. A. Evans, J. Bartoli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129;
79. b) W. Richter, W. Sucrow, Chem. Ber. 1971, 104, 3679-3682.
80. a) W. S. Johnson, V. J. Bauer, J. L. Margrave, M. A. Frisch, L. H. Dreger, W. N. Hubbard, J. Am. Chem. Soc. 1961, 83, 606-614;
81. b) P. Vittorelli, H.-J. Hansen, H. Schmid, Helv. Chim. Acta 1975, 58, 1293-1309;
82. c) R. L. Vance, N. G. Rondan, K. N. Houk, F. Jensen, W. T. Borden, A. Komornicki, E. Wimmer, J. Am. Chem. Soc. 1988, 110, 2314-2315;
83. d) G. Büchi, J. E. Powell, J. Am. Chem. Soc. 1970, 92, 3162-3133;
84. e) M. M. Abelmann, R. F. Funk, J. D. Munger, J. Am. Chem. Soc. 1982, 104, 4030-4032.
85. D. J. Peterson, J. Org. Chem. 1968, 33, 780-784.
86. E. Negishi, D. R. Swanson, C. J. Rousset, J. Org. Chem. 1990, 55, 5406-5409.
87. a) G. A. Olah, V. P. Reddy, G. A. S. Prakash, Synthesis 1991, 29-30;
88. b) J. W. Benbow, K. F. McClure, S. J. Danishefsky, J. Am. Chem. Soc. 1993, 115, 12305-12314;
89. c) Z. Wang, L. S. Jimenez, Tetrahedron Lett. 1996, 37, 6049-6052.
90. a) D. C. Lankin, S. T. Nugent, S. N. Rao, Carbohydr. Res. 1993, 244, 49-68;
91. b) M. Harmata, D. E. Jones, J. Org. Chem. 1997, 62, 1578-1579.
92. J. A. Marshall, W. J. DuBay, J. Org. Chem. 1993, 58, 3435-3443.
93. Y. Tamaru, T. Harada, S. Nishi, Z. Yoshida, Tetrahedron Lett. 1982, 23, 2383-2386.
94. The NOESY displayed the same cross-peaks as reported for carbinols 21 and 31 (Figure 3).
95. a) A. Fürstner, Angew. Chem. Int. Ed. Engl. 2000, 39, 3012-3043; Angew. Chem. 2000, 112, 3140-3172;
96. a) A. Fürstner, Angew. Chem. Int. Ed. Engl. 2000, 39, 3012-3043; Angew. Chem. 2000, 112, 3140-3172;
97. b) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450;
98. c) B. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 1997, 36, 2037-2056; Angew. Chem. 199 7, 109, 2124-2144;
99. c) B. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 1997, 36, 2037-2056; Angew. Chem. 199 7, 109, 2124-2144;
100. d) A. Fürstner, Top. Catal. 1997, 4, 285-299;
101. e) S. K. Amstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388;
102. f) C. Pariya, K. N. Jayaprakash, A. Sarkar, Coord. Chem. Rev. 1998, 168, 1-48;
103. g) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452;
104. h) H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 1995, 34, 1833-1836; Angew. Chem. 1995, 107, 1981-1984;
105. h) H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 1995, 34, 1833-1836; Angew. Chem. 1995, 107, 1981-1984;
106. i) K. J. Ivin, J. Mol. Catal. A. 1998, 133, 1-16;
107. j) M. L. Randall, M. L. Snapper, J. Mol. Catal. A. 1998, 133, 29-40;
108. k) A. S. K. Hashmi, J. Prakt. Chem. 1997, 339, 195-199;
109. l) A. J. Phillips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-89.
110. The decomposition led to diverse products which could not be separated. Any smooth aromatization had not been observed.
111. E. Wenkert, T. E. Goodwin, Synth. Commun. 1977, 7, 409-415.
112. S. H. Wu, Z. B. Ding, Synth. Commun. 1994, 24, 2173-2178.
113. T. Kametani, H. Kondoh, T. Honda, H. Ishizone, Y. Suzuki, W. Mori, Chem. Lett. 1989, 901-904.