A versatile stereocontrolled approach to chiral tetrahydrofuran and tetrahydropyran derivatives by use of sequential asymmetric Horner-Wadsworth-Emmons and ring-closure reactions

Journal of Organic Chemistry

Volumn 67, Issue 21, 2002, Pages 7226-7237

  Vares, Lauri ^a,b,c   Rein, Tobias ^a,d  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

^c ASTRAZENECA R AND D   (Sweden)

^d ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL TETRAHYDROFURAN;

CATALYSIS; PALLADIUM; STEREOCHEMISTRY;

ORGANIC CHEMICALS;

EPOXIDE; PALLADIUM; TETRAHYDROFURAN; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

ALDEHYDES; FURANS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRANS; STEREOISOMERISM;

EID: 0037131320     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0259111     Document Type: Article

References (73)

1. For a recent review, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504.
2. Wesley, J. W. Polyether Antibiotics: Naturally Occurring Acid Ionophores; Marcel Dekker: New York, 1982; Vols. I and II.
3. Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041.
4. Corley, D. G.; Herb, R.; Moore, R. E.; Scheuer, P. J.; Paul, V. J. J. Org. Chem. 1988, 53, 3644.
5. Sakemi, S.; Higa, T.; Jefford, C. W.; Bernardinelli, G. Tetrahedron Lett. 1986, 27, 4287.
6. Shi, G.; Alfonso, D.; Fatope, M. O.; Zeng, L.; Gu, Z.-M.; Zhao, G.-X.; He, K.; MacDougal, J. M.; McLaughlin, J. L. J. Am. Chem. Soc. 1995, 117, 10409.
7. (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
8. (b) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711.
9. (c) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175.
10. (a) Bartlett, P. A.; Chapuis, C. J. Org. Chem. 1986, 51, 2799.
11. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335.
12. (c) Iqbal, J.; Pandey, A.; Chauhan, B. P. S. Tetrahedron 1991, 47, 4143.
13. (d) Fotsch, C. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4141.
14. (e) Maguire, R. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1995, 2487.
15. (f) Li, K.; Vig, S.; Uckun, F. M. Tetrahedron Lett. 1998, 39, 2063.
16. (g) Ley, S. V.; Brown, D. S.; Clase, J. A.; Fairbanks, A. J.; Lennon, I. C.; Osborn, H. M. I.; Stokes (née Owen), E. S. E.; Wadsworth, D. J. J. Chem. Soc., Perkin Trans. 1 1998, 2259.
17. (a) Banwell, M. G.; Bui, C. T.; Pham, H. T. T.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1 1996, 967.
18. (b) Takagi, R.; Sasaoka, A.; Kojima, S.; Ohkata, K. Heterocycles 1997, 45, 2313.
19. (c) Betancort, J. M.; Martín, V. S.; Padrón, J. M.; Palazón, J. M.; Ramírez, M. A.; Soler, M. A. J. Org. Chem. 1997, 62, 4570, and references therein.
20. (d) Ramírez, M. A.; Padrón, J. M.; Palazón, J. M.; Martín, V. S. J. Org. Chem. 1997, 62, 4584.
21. (e) Paterson, I.; Arnott, E. A. Tetrahedron Lett. 1998, 39, 7185.
22. For examples using Pd(II), see: (a) Semmelhack, M. F.; Epa, W. R.; Cheung, A. W.-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455, and references therein. For recent examples using Re(VII), see: (b) Kennedy, R. M.; Tang, S. Tetrahedron Lett. 1992, 33, 3729. (c) Towne, T. B.; McDonald, F. E. J. Am. Chem. Soc. 1997, 119, 6022. (d) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014. (e) Sinha, S. C.; Keinan, E.; Sinha, S. C. J. Am. Chem. Soc. 1998, 120, 9076. (f) Morimoto, Y.; Iwai, T.; Kinoshita, T. J. Am. Chem. Soc. 1999, 121, 6792 and references therein.
23. For examples using Pd(II), see: (a) Semmelhack, M. F.; Epa, W. R.; Cheung, A. W.-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455, and references therein. For recent examples using Re(VII), see: (b) Kennedy, R. M.; Tang, S. Tetrahedron Lett. 1992, 33, 3729. (c) Towne, T. B.; McDonald, F. E. J. Am. Chem. Soc. 1997, 119, .6022. (d) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014. (e) Sinha, S. C.; Keinan, E.; Sinha, S. C. J. Am. Chem. Soc. 1998, 120, 9076. (f) Morimoto, Y.; Iwai, T.; Kinoshita, T. J. Am. Chem. Soc. 1999, 121, 6792 and references therein.
24. For examples using Pd(II), see: (a) Semmelhack, M. F.; Epa, W. R.; Cheung, A. W.-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455, and references therein. For recent examples using Re(VII), see: (b) Kennedy, R. M.; Tang, S. Tetrahedron Lett. 1992, 33, 3729. (c) Towne, T. B.; McDonald, F. E. J. Am. Chem. Soc. 1997, 119, 6022. (d) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014. (e) Sinha, S. C.; Keinan, E.; Sinha, S. C. J. Am. Chem. Soc. 1998, 120, 9076. (f) Morimoto, Y.; Iwai, T.; Kinoshita, T. J. Am. Chem. Soc. 1999, 121, 6792 and references therein.
25. For examples using Pd(II), see: (a) Semmelhack, M. F.; Epa, W. R.; Cheung, A. W.-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455, and references therein. For recent examples using Re(VII), see: (b) Kennedy, R. M.; Tang, S. Tetrahedron Lett. 1992, 33, 3729. (c) Towne, T. B.; McDonald, F. E. J. Am. Chem. Soc. 1997, 119, 6022. (d) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014. (e) Sinha, S. C.; Keinan, E.; Sinha, S. C. J. Am. Chem. Soc. 1998, 120, 9076. (f) Morimoto, Y.; Iwai, T.; Kinoshita, T. J. Am. Chem. Soc. 1999, 121, 6792 and references therein.
26. For examples using Pd(II), see: (a) Semmelhack, M. F.; Epa, W. R.; Cheung, A. W.-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455, and references therein. For recent examples using Re(VII), see: (b) Kennedy, R. M.; Tang, S. Tetrahedron Lett. 1992, 33, 3729. (c) Towne, T. B.; McDonald, F. E. J. Am. Chem. Soc. 1997, 119, 6022. (d) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014. (e) Sinha, S. C.; Keinan, E.; Sinha, S. C. J. Am. Chem. Soc. 1998, 120, 9076. (f) Morimoto, Y.; Iwai, T.; Kinoshita, T. J. Am. Chem. Soc. 1999, 121, 6792 and references therein.
27. For examples using Pd(II), see: (a) Semmelhack, M. F.; Epa, W. R.; Cheung, A. W.-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455, and references therein. For recent examples using Re(VII), see: (b) Kennedy, R. M.; Tang, S. Tetrahedron Lett. 1992, 33, 3729. (c) Towne, T. B.; McDonald, F. E. J. Am. Chem. Soc. 1997, 119, 6022. (d) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014. (e) Sinha, S. C.; Keinan, E.; Sinha, S. C. J. Am. Chem. Soc. 1998, 120, 9076. (f) Morimoto, Y.; Iwai, T.; Kinoshita, T. J. Am. Chem. Soc. 1999, 121, 6792 and references therein.
28. Kotsuki, H. Synlett 1992, 97 and references therein.
29. Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148.
30. (a) Oikawa, M.; Ueno, T.; Oikawa, H.; Ichihara, A. J. Org. Chem. 1995, 60, 5048.
31. (b) Crimmins, M. T.; Rafferty, S. W. Tetrahedron Lett. 1996, 37, 5649.
32. (a) Berninger, J.; Koert, U.; Eisenberg-Höhl, C.; Knochel, P. Chem. Ber. 1995, 128, 1021 and references therein.
33. (b) Wang, Z.-M.; Shen, M. J. Org. Chem. 1998, 63, 1414.
34. (a) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461 and references therein.
35. (b) Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868.
36. (a) Tömösközi, I.; Janszó, G. Chem. Ind. (London) 1962, 2085.
37. (b) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369.
38. (c) Rein, T.; Pedersen, T. M. Synthesis 2002, 579.
39. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
40. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
41. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
42. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
43. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
44. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
45. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
46. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
47. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
48. Asymmetric HWE reactions with dicarbonyl substrates: (d) Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699. (e) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929. (f) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802. (g) Tanaka, K.; Ohta, Y.; Fuji, K.; Taga, T. Tetrahedron Lett. 1993, 34, 4071. (h) Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847. (i) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (j) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (k) Rein, T.; Vares, L.; Kawasaki, I.; Pedersen, T. M.; Norrby, P.-O.; Brandt, P.; Tanner, D. Phosphorus, Sulfur Silicon 1999, 144-148, 169. (l) Tanaka, K.; Watanabe, T.; Shimamoto, K.-Y.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599. (m) Vares, L.; Rein, T. Org. Lett. 2000, 2, 2611.
49. Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; John Wiley & Sons: Chichester, 1995.
50. Part of this work has been reported in earlier communications; see ref 16k,m.
51. (a) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723.
52. (b) Shimizu, I.; Oshima, M.; Nisar, M.; Tsuji, J. Chem. Lett. 1986, 1775.
53. (c) Sugiura, M.; Yagi, Y.; Wei, S.-Y.; Nakai, T. Tetrahedron Lett. 1998, 39, 4351.
54. (d) Noguchi, Y.; Yamada, T.; Uchiro, H.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 7493, and references therein.
55. (a) Bäckvall, J. E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
56. (b) Bäckvall, J.-E.; Granberg, K. L.; Hopkins, R. B. Acta Chem. Scand. 1990, 44, 492.
57. (a) Shing, T. K. M.; Tam, E. K. W.; Tai, W.-F.; Chung, I. H. F.; Jiang, Q. Chem. Eur. J. 1996, 2, 50.
58. (b) Shing, T. K. M.; Tam, E. K. W. Tetrahedron Lett. 1999, 40, 2179.
59. The primary alcohols recovered after the acyl group migration could be converted to mixtures of secondary/primary alcohols again, thereby increasing the overall yield of the desired secondary alcohol.
60. (a) Sjögren, M. P. T.; Hansson, S.; Norrby, P.-O.; Åkermark, B.; Cucciolito, M. E.; Vitagliano, A. Organometallics 1992, 11, 3954.
61. (b) Sjögren, M. P. T.; Hansson, S.; Akermark, B.; Vitagliano, A. Organometallics 1994, 13, 1963.
62. 4 in combination with i-PrOH/THF resulted in much faster protective group migration during the reduction compared to when MeOH/THF was used as solvent mixture.
63. The ring-closed product 30 was obtained in diastereomerically pure form, even though the starting material contained 5% of minor diastereomer 45 (see the Experimental Section).
64. For a review on epoxide openings, see: Smith, J. K. Synthesis 1984, 629.
65. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
66. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092, and references therein. For details regarding the NMR analyses of the Mosher esters 41 and 42, see the Supporting Information.
67. 13C NMR peaks at 73.8 and 68.5 ppm, respectively, whereas the corresponding carbons in the minor product 35 give peaks at 79.2 and 72.2 ppm, respectively. In 2,6-trans-THP derivatives the carbons at C-2 and C-6 are, on average, shifted upfield by ca. 7 ppm compared to the same carbons in the corresponding 2,6-cis-THP derivative; see: (a) Pihlaja, K.; Kleinpeter, E. Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis; VCH Publishers: New York, 1994; pp 108-114. (b) Eliel, E. L.; Manoharan, M.; Pietrusiewicz, K. M.; Hargrave, K. D. Org. Magn. Reson. 1983, 21, 94.
68. 13C NMR peaks at 73.8 and 68.5 ppm, respectively, whereas the corresponding carbons in the minor product 35 give peaks at 79.2 and 72.2 ppm, respectively. In 2,6-trans-THP derivatives the carbons at C-2 and C-6 are, on average, shifted upfield by ca. 7 ppm compared to the same carbons in the corresponding 2,6-cis-THP derivative; see: (a) Pihlaja, K.; Kleinpeter, E. Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis; VCH Publishers: New York, 1994; pp 108-114. (b) Eliel, E. L.; Manoharan, M.; Pietrusiewicz, K. M.; Hargrave, K. D. Org. Magn. Reson. 1983, 21, 94.
69. The cis and trans isomers could be separated by careful flash chromatography (2-8% EtOAc in hexanes).
70. 1H NMR.
71. Compound 44 originates from 16b, the minor diastereomer formed in the reaction between 13b and 14a.
72. Compound 45 originates from the minor (E)-diastereomer formed in the asymmetric HWE reaction with 27a.
73. We cannot exclude the possibility that the product contains trace amounts of the 2,6-trans-THP product resulting from ring closure of compound 44; we have only been able to detect product isomers 34 and 35, however.