Concise and stereoselective synthesis of enamides and dienamides by a titanium-mediated coupling method

Organic Letters

Volumn 5, Issue 1, 2003, Pages 67-70

  Tanaka, Ryoichi ^a   Hirano, Shuji ^a   Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKYNE; AMIDE; CYCLOPENTADIENE DERIVATIVE; DIENAMIDE DERIVATIVE; ENAMIDE DERIVATIVE; KETONE DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; HYDROLYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037884003     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027209x     Document Type: Article

References (57)

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2. General: Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vols. 1-7. Enol silyl ethers: Fleming I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Pawlenko, S. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 404-462. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; pp 206-272. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; pp 198-287. Enol esters: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 1-117. Enol ethers: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 140-349.
3. General: Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vols. 1-7. Enol silyl ethers: Fleming I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Pawlenko, S. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 404-462. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; pp 206-272. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; pp 198-287. Enol esters: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 1-117. Enol ethers: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 140-349.
4. General: Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vols. 1-7. Enol silyl ethers: Fleming I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Pawlenko, S. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 404-462. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; pp 206-272. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; pp 198-287. Enol esters: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 1-117. Enol ethers: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 140-349.
5. General: Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vols. 1-7. Enol silyl ethers: Fleming I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Pawlenko, S. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 404-462. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; pp 206-272. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; pp 198-287. Enol esters: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 1-117. Enol ethers: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 140-349.
6. General: Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vols. 1-7. Enol silyl ethers: Fleming I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Pawlenko, S. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 404-462. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; pp 206-272. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; pp 198-287. Enol esters: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 1-117. Enol ethers: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 140-349.
7. General: Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vols. 1-7. Enol silyl ethers: Fleming I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Pawlenko, S. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 404-462. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; pp 206-272. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; pp 198-287. Enol esters: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 1-117. Enol ethers: Frauenrath, H. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/1, pp 140-349.
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12. Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489-492. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255-1256. Witulski, B.; Gössmann, M. Chem. Commun. 1999, 1879-1880. For reviews, see: Himbert, G. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/3, pp 3267-3443. Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89-131.
13. Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489-492. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255-1256. Witulski, B.; Gössmann, M. Chem. Commun. 1999, 1879-1880. For reviews, see: Himbert, G. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/3, pp 3267-3443. Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89-131.
14. Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489-492. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255-1256. Witulski, B.; Gössmann, M. Chem. Commun. 1999, 1879-1880. For reviews, see: Himbert, G. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Kropf, H., Schaumann, E., Eds.; Thieme: Stuttgart, 1993; Vol. E15/3, pp 3267-3443. Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89-131.
15. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886. Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834. Eisch, J. J. J. Organomet. Chem. 2001, 617-618, 148-157. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759-784. Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354.
16. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886. Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834. Eisch, J. J. J. Organomet. Chem. 2001, 617-618, 148-157. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759-784. Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354.
17. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886. Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834. Eisch, J. J. J. Organomet. Chem. 2001, 617-618, 148-157. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759-784. Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354.
18. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886. Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834. Eisch, J. J. J. Organomet. Chem. 2001, 617-618, 148-157. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759-784. Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354.
19. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886. Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834. Eisch, J. J. J. Organomet. Chem. 2001, 617-618, 148-157. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759-784. Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354.
20. For reviews on acetylene-metal complexes, see the following. Ti and Zr: ref 4. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769. Nb and Ta: Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981. Hartung, J. B., Jr.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 5468-5469. Strickler, J. R.; Bruck, M. A.; Wexler, P. A.; Wigley, D. E. Organometallics 1990, 9, 266-273.
21. For reviews on acetylene-metal complexes, see the following. Ti and Zr: ref 4. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769. Nb and Ta: Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981. Hartung, J. B., Jr.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 5468-5469. Strickler, J. R.; Bruck, M. A.; Wexler, P. A.; Wigley, D. E. Organometallics 1990, 9, 266-273.
22. For reviews on acetylene-metal complexes, see the following. Ti and Zr: ref 4. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769. Nb and Ta: Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981. Hartung, J. B., Jr.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 5468-5469. Strickler, J. R.; Bruck, M. A.; Wexler, P. A.; Wigley, D. E. Organometallics 1990, 9, 266-273.
23. For reviews on acetylene-metal complexes, see the following. Ti and Zr: ref 4. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769. Nb and Ta: Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981. Hartung, J. B., Jr.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 5468-5469. Strickler, J. R.; Bruck, M. A.; Wexler, P. A.; Wigley, D. E. Organometallics 1990, 9, 266-273.
24. For reviews on acetylene-metal complexes, see the following. Ti and Zr: ref 4. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769. Nb and Ta: Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981. Hartung, J. B., Jr.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 5468-5469. Strickler, J. R.; Bruck, M. A.; Wexler, P. A.; Wigley, D. E. Organometallics 1990, 9, 266-273.
25. For reviews on acetylene-metal complexes, see the following. Ti and Zr: ref 4. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769. Nb and Ta: Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981. Hartung, J. B., Jr.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 5468-5469. Strickler, J. R.; Bruck, M. A.; Wexler, P. A.; Wigley, D. E. Organometallics 1990, 9, 266-273.
26. For reviews on acetylene-metal complexes, see the following. Ti and Zr: ref 4. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769. Nb and Ta: Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981. Hartung, J. B., Jr.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 5468-5469. Strickler, J. R.; Bruck, M. A.; Wexler, P. A.; Wigley, D. E. Organometallics 1990, 9, 266-273.
27. Quite recently, generation and reactions of acetylenic phosphonate-zirconocene complexes were reported: Quntar, A. A. A.; Srebnik, M. Org. Lett. 2001, 3, 1379-1381. Quntar, A. A. A.; Srebnik, M. J. Org. Chem. 2001, 66, 6650-6653. Quntar, A. A. A.; Melman, A.; Srebnik, M. Synlett 2002, 61-64.
28. Quite recently, generation and reactions of acetylenic phosphonate-zirconocene complexes were reported: Quntar, A. A. A.; Srebnik, M. Org. Lett. 2001, 3, 1379-1381. Quntar, A. A. A.; Srebnik, M. J. Org. Chem. 2001, 66, 6650-6653. Quntar, A. A. A.; Melman, A.; Srebnik, M. Synlett 2002, 61-64.
29. Quite recently, generation and reactions of acetylenic phosphonate-zirconocene complexes were reported: Quntar, A. A. A.; Srebnik, M. Org. Lett. 2001, 3, 1379-1381. Quntar, A. A. A.; Srebnik, M. J. Org. Chem. 2001, 66, 6650-6653. Quntar, A. A. A.; Melman, A.; Srebnik, M. Synlett 2002, 61-64.
30. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
31. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
32. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
33. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
34. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
35. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
36. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
37. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
38. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
39. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N. ; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408. Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414. Ogawa, T. ; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
40. Stereoselective preparation of trisubstituted enamides of type 7, which have two different β-alkyl (and -silyl) substituents, appears to be quite difficult. On the contrary, trisubstituted enamides having the same two β-substituents have been reported. Meuzelaar, G. J.; van Vliet, M. C. A.; Neeleman, E.; Maat, L.; Sheldon, R. A. Liebigs Ann./Recl 1997, 1159-1163. Murai, T.; Kasai, Y.; Ishihara, H.; Kato, S. J. Org. Chem. 1992, 57, 5542-5545. Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697-6703. Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139-2145.
41. Stereoselective preparation of trisubstituted enamides of type 7, which have two different β-alkyl (and -silyl) substituents, appears to be quite difficult. On the contrary, trisubstituted enamides having the same two β-substituents have been reported. Meuzelaar, G. J.; van Vliet, M. C. A.; Neeleman, E.; Maat, L.; Sheldon, R. A. Liebigs Ann./Recl 1997, 1159-1163. Murai, T.; Kasai, Y.; Ishihara, H.; Kato, S. J. Org. Chem. 1992, 57, 5542-5545. Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697-6703. Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139-2145.
42. Stereoselective preparation of trisubstituted enamides of type 7, which have two different β-alkyl (and -silyl) substituents, appears to be quite difficult. On the contrary, trisubstituted enamides having the same two β-substituents have been reported. Meuzelaar, G. J.; van Vliet, M. C. A.; Neeleman, E.; Maat, L.; Sheldon, R. A. Liebigs Ann./Recl 1997, 1159-1163. Murai, T.; Kasai, Y.; Ishihara, H.; Kato, S. J. Org. Chem. 1992, 57, 5542-5545. Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697-6703. Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139-2145.
43. Stereoselective preparation of trisubstituted enamides of type 7, which have two different β-alkyl (and -silyl) substituents, appears to be quite difficult. On the contrary, trisubstituted enamides having the same two β-substituents have been reported. Meuzelaar, G. J.; van Vliet, M. C. A.; Neeleman, E.; Maat, L.; Sheldon, R. A. Liebigs Ann./Recl 1997, 1159-1163. Murai, T.; Kasai, Y.; Ishihara, H.; Kato, S. J. Org. Chem. 1992, 57, 5542-5545. Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697-6703. Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139-2145.
44. For the preparation of cyclic enamides from ynamides, see: Witulski, B.; Gössmann, M. Synlett 2000, 1793-1797. Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272-7276.
45. For the preparation of cyclic enamides from ynamides, see: Witulski, B.; Gössmann, M. Synlett 2000, 1793-1797. Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272-7276.
46. See Supporting Information.
47. For synthetic application of organotitanium compounds, see: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 139-172. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, UK, 1994; pp 195-282.
48. For synthetic application of organotitanium compounds, see: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 139-172. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, UK, 1994; pp 195-282.
49. For synthetic application of organotitanium compounds, see: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 139-172. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, UK, 1994; pp 195-282.
50. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley: New York, 1990.
51. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206
52. For reported preparation of 1-amino-1,3-butadiene derivatives, see: Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352-2354 and 8295. Overman, L. E.; Taylor, G. F.; Petty, C. B.; Jessup, P. J. J. Org. Chem. 1978, 43, 2164-2167. Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047. Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166. Huang, Y.; Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163-1166 and references therein.
53. For reported preparation of 1-amino-1,3-butadiene derivatives, see: Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352-2354 and 8295. Overman, L. E.; Taylor, G. F.; Petty, C. B.; Jessup, P. J. J. Org. Chem. 1978, 43, 2164-2167. Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047. Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166. Huang, Y.; Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163-1166 and references therein.
54. For reported preparation of 1-amino-1,3-butadiene derivatives, see: Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352-2354 and 8295. Overman, L. E.; Taylor, G. F.; Petty, C. B.; Jessup, P. J. J. Org. Chem. 1978, 43, 2164-2167. Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047. Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166. Huang, Y.; Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163-1166 and references therein.
55. For reported preparation of 1-amino-1,3-butadiene derivatives, see: Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352-2354 and 8295. Overman, L. E.; Taylor, G. F.; Petty, C. B.; Jessup, P. J. J. Org. Chem. 1978, 43, 2164-2167. Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047. Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166. Huang, Y.; Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163-1166 and references therein.
56. For reported preparation of 1-amino-1,3-butadiene derivatives, see: Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352-2354 and 8295. Overman, L. E.; Taylor, G. F.; Petty, C. B.; Jessup, P. J. J. Org. Chem. 1978, 43, 2164-2167. Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047. Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166. Huang, Y.; Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163-1166 and references therein.
57. For our previous effort to make nonfunctionalized or electron-deficient dienes, see: Hamada, T.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1999, 121, 7342-7344.