Transition metal-catalyzed [5 + 2] cycloadditions of allenes and vinylcyclopropanes: First studies of endo-exo selectivity, chemoselectivity, relative stereochemistry, and chirality transfer

Journal of the American Chemical Society

Volumn 121, Issue 22, 1999, Pages 5348-5349

  Wender, Paul A ^a   Glorius, Frank ^a   Husfeld, Craig O ^a   Langkopf, Elke ^a   Love, Jennifer A ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CYCLOPROPANE; PHORBOL ESTER;

ARTICLE; BINDING AFFINITY; CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; INFRARED SPECTROPHOTOMETRY; LIGAND BINDING; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033538287     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9903072     Document Type: Article

References (35)

1. [4 + 4] Cycloadditions: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4 + 2] Cycloadditions: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255- 1275.
2. [4 + 4] Cycloadditions: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4 + 2] Cycloadditions: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255- 1275.
3. [4 + 4] Cycloadditions: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4 + 2] Cycloadditions: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255- 1275.
4. [4 + 4] Cycloadditions: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4 + 2] Cycloadditions: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255- 1275.
5. [4 + 4] Cycloadditions: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4 + 2] Cycloadditions: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255- 1275.
6. [4 + 4] Cycloadditions: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4 + 2] Cycloadditions: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255- 1275.
7. [4 + 4] Cycloadditions: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4 + 2] Cycloadditions: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255- 1275.
8. [4 + 4] Cycloadditions: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4 + 2] Cycloadditions: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
9. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
10. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A., J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220.
11. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A., J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220.
12. For additional information pertaining to possible mechanistic pathways, see refs 2 and 3.
13. For lead references and total synthesis, see: Evans, F. J., Ed. Naturally Occurring Phorbol Esters; CRC Press: Boca Raton, FL, 1986. Hecker, E.; Schmidt, R. Fortschr. Chem. Org. Naturst. 1974, 31, 377. Wender, P. A.; Kogen, H.; Lee, H-Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
14. For lead references and total synthesis, see: Evans, F. J., Ed. Naturally Occurring Phorbol Esters; CRC Press: Boca Raton, FL, 1986. Hecker, E.; Schmidt, R. Fortschr. Chem. Org. Naturst. 1974, 31, 377. Wender, P. A.; Kogen, H.; Lee, H-Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
15. For lead references and total synthesis, see: Evans, F. J., Ed. Naturally Occurring Phorbol Esters; CRC Press: Boca Raton, FL, 1986. Hecker, E.; Schmidt, R. Fortschr. Chem. Org. Naturst. 1974, 31, 377. Wender, P. A.; Kogen, H.; Lee, H-Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
16. For lead references and total synthesis, see: Evans, F. J., Ed. Naturally Occurring Phorbol Esters; CRC Press: Boca Raton, FL, 1986. Hecker, E.; Schmidt, R. Fortschr. Chem. Org. Naturst. 1974, 31, 377. Wender, P. A.; Kogen, H.; Lee, H-Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
17. For lead references and total synthesis, see: Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977.
18. For general references to metal-catalyzed cycloadditions and seven-membered ring synthesis, see: refs 1-3. Nola, E.; Dzwiniel, T. L.; Schweibert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1998, 120, 9702-9703. Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609. Wender, P. A.; Love, J. A. Adv. Cycloaddit., 1999, 1-45.
19. For general references to metal-catalyzed cycloadditions and seven- membered ring synthesis, see: refs 1-3. Nola, E.; Dzwiniel, T. L.; Schweibert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1998, 120, 9702-9703. Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609. Wender, P. A.; Love, J. A. Adv. Cycloaddit., 1999, 1-45.
20. For general references to metal-catalyzed cycloadditions and seven- membered ring synthesis, see: refs 1-3. Nola, E.; Dzwiniel, T. L.; Schweibert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1998, 120, 9702-9703. Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609. Wender, P. A.; Love, J. A. Adv. Cycloaddit., 1999, 1-45.
21. For recent examples of metal-catalyzed reactions of allenes, see: Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4-5. Xiao, W. J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609- 2612. Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931-934. Hashmi, A.; Ruppert, T. L.; Knofel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295-7304. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
22. For recent examples of metal-catalyzed reactions of allenes, see: Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4-5. Xiao, W. J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609-2612. Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931-934. Hashmi, A.; Ruppert, T. L.; Knofel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295-7304. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
23. For recent examples of metal-catalyzed reactions of allenes, see: Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4-5. Xiao, W. J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609- 2612. Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931-934. Hashmi, A.; Ruppert, T. L.; Knofel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295-7304. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
24. For recent examples of metal-catalyzed reactions of allenes, see: Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4-5. Xiao, W. J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609- 2612. Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931-934. Hashmi, A.; Ruppert, T. L.; Knofel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295-7304. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
25. For recent examples of metal-catalyzed reactions of allenes, see: Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4-5. Xiao, W. J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609- 2612. Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931-934. Hashmi, A.; Ruppert, T. L.; Knofel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295-7304. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
26. Substrate 1 is prepared in 81% yield by alkylation of dimethyl 2-(3′-cyclopropyl-2′-propen-1′-yl)-malonate with methanesulfonic acid 5,5-dimethylhexa-2,3-dienyl ester. The mesylate is derived from 5,5-dimethyl-hexa-2,3-dien-1-ol, which is prepared by the method of Lang and Hansen: Lang, R. W.; Hansen, H-J. Org. Synth. 1984, 202. Details are provided in the Supporting Information.
27. In a representative procedure, tris(triphenylphosphine)rhodium(I) chloride (0.1mol %) is added in one batch to a base-washed, oven-dried Schlenk flask under an argon atmosphere and is dissolved in freshly distilled, oxygen-free toluene (1.0 mL). The solution is stirred for 5 min at room temperature, after which ene-vinylcyclopropane 1 (42.3 mg, 0.132 mmol in 0.3 mL of toluene) is added over 10 s, and the solution is heated to 110 °C for 5 h. After cooling, the reaction mixture is filtered through a plug of alumina and concentrated. HPLC analysis of this mixture indicates that 2 is formed with >99% selectivity. Flash chromatography (silica gel, 10% ethyl acetate in hexane) gives cycloadduct 2 in 96% yield as a colorless oil.
28. Details of the X-ray data for 2 are provided in the Supporting Information.
29. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165.
30. The stereochemistry of 4a was assigned on the basis of the nOe exhibited between the ring junction hydrogens. The stereochemistry of ring fusion isomer 4b follows from this assignment.
31. The stereochemistries of 7a and 7b were determined by correlation with the monodecarboxylation products of 4b and 2, respectively.
32. The cis-ring fusion stereochemistry of 9 was assigned by analogy to 2, 4a, 5a, 7a, and 7b.
33. The stereochemistry of 11 was assigned on the basis of the nOe exhibited between the angular methyl and the ring junction hydrogen.
34. Chiral 1 was prepared as described in ref 8 using a chiral mesylate prepared by the method of Carreira: Carreira, E. M.; Hastings, C. A.; Shephard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc. 1994, 116, 6622-6630.
35. The enantiomeric excesses of 1 and 2 were determined using chiral HPLC analysis (CHIRALPAK-AD column). Details are provided in the Supporting Information.