Highly Stereoselective Alk-2-enylation of Aldehyde via Allyl-Transfer Reaction

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 61, Issue 10, 2003, Pages 992-1001

  Nokami, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Alk 2 enylation; Allyl transfer reaction; Asymmetric synthesis; Homoallylic alcohol; Menthone; Six membered cyclic transition state; 3.3 sigmatropic rearrangement; adduct

Indexed keywords

ALCOHOLS; KETONES; OPTICAL PROPERTIES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALLYLATION; REGIOSELECTIVITY;

ALDEHYDES;

EID: 0346329837     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.61.992     Document Type: Article

References (32)

1. K. Sisido, Y. Takeda, J. Org. Chem., 26, 2301 (1961)
2. J. Nokami, J. Otera, T. Sudo, R. Okawara, Organometallics, 2, 191 (1983)
3. J. Nokami, S. Wakabayashi, R. Okawara, Chem. Lett., 1984, 869
4. (a) J. Nokami, T. Tamaoka, H. Ogawa, S. Wakabayashi, Chem. Lett., 1986, 541
5. (b) T. Mandai, J. Nokami, T. Yano, S. Yoshinaga, J. Otera, J. Org. Chem., 49, 172 (1984)
6. A. Gambaro, A. Boaretto, D. Marton, G. Tagliavini, J. Organometal. Chem., 254, 293 (1983); Z. Y. Wei, J. S. Li, D. Wang, T. H. Chan, Tetrahedron Lett., 28, 3441 (1987); L. Coppi, A. Ricci, M. Taddei, ibid., 28, 973 (1987); A. Mekhalfia, E. I. Markó, H. Adams, ibid., 32, 4783 (1991)
7. A. Gambaro, A. Boaretto, D. Marton, G. Tagliavini, J. Organometal. Chem., 254, 293 (1983); Z. Y. Wei, J. S. Li, D. Wang, T. H. Chan, Tetrahedron Lett., 28, 3441 (1987); L. Coppi, A. Ricci, M. Taddei, ibid., 28, 973 (1987); A. Mekhalfia, E. I. Markó, H. Adams, ibid., 32, 4783 (1991)
8. A. Gambaro, A. Boaretto, D. Marton, G. Tagliavini, J. Organometal. Chem., 254, 293 (1983); Z. Y. Wei, J. S. Li, D. Wang, T. H. Chan, Tetrahedron Lett., 28, 3441 (1987); L. Coppi, A. Ricci, M. Taddei, ibid., 28, 973 (1987); A. Mekhalfia, E. I. Markó, H. Adams, ibid., 32, 4783 (1991)
9. A. Gambaro, A. Boaretto, D. Marton, G. Tagliavini, J. Organometal. Chem., 254, 293 (1983); Z. Y. Wei, J. S. Li, D. Wang, T. H. Chan, Tetrahedron Lett., 28, 3441 (1987); L. Coppi, A. Ricci, M. Taddei, ibid., 28, 973 (1987); A. Mekhalfia, E. I. Markó, H. Adams, ibid., 32, 4783 (1991)
10. J. Nokami, K. Yoshizane, H. Matsuura, S. Sumida, J. Am. Chem. Soc., 120, 6609 (1998)
11. (a) A. Yanagisawa, S. Habaue, H. Yamamoto, J. Am. Chem. Soc., 113, 8955 (1991)
12. (b) A. Yanagisawa, S. Habaue, K. Yasue, H. Yamamoto, ibid., 116, 6130 (1994)
13. (a) S. Sumida, M. Ohga, J. Mitani, J. Nokami, J. Am. Chem. Soc., 122, 1310 (2000)
14. (b) J. Nokami, L. Anthony, S. Sumida, Chem. Eur. J., 6, 2909 (2000)
15. W. R. Roush, K. Ando, D. B. Powers, R. L. Halterman, A. D. Palkowitz, Tetrahedron Lett., 29, 5579 (1988)
16. Y. Yamamoto, H. Yatagai, Y. Naruta, K. Maruyama, J. Am. Chem. Soc., 102, 7109 (1980)
17. Y. Naruta, Y. Nishigaichi, K. Maruyama, Tetrahedron, 45, 1067 (1989)
18. (a) A. Gambaro, P. Gains, D. Marton, V. Peruzzo, G. Tagliavini, J. Organometal. Chem., 231, 307 (1982)
19. (b) G. E. Keck, D. E. Abbott, E. P. Boden, E. J. Enholm, Tetrahedron Lett., 25, 3927 (1984)
20. (c) H. Miyake, K. Yamamura, Chem. Lett., 1992, 1369
21. (d) T. P. Loh, X. R. Li, Angew. Chem., Int. Ed., 36, 980 (1997)
22. J. Nokami, M. Ohga, H. Nakamoto, T. Matsubara, I. Hussain, K. Kataoka, J. Am. Chem. Soc., 123, 9168 (2001)
23. J. Nokami, K. Nomiyama, S. Matsuda, N. Imai, K. Kataoka, Angew. Chem., Int. Ed., 42, 1273 (2003)
24. I. Hussain, T. Komasaka, M. Ohga, J. Nokami, Synlett, 2002, 640
25. T.-P. Loh, Q.-Y. Hu, L.-T. Ma, J. Am. Chem. Soc., 123, 2450 (2001); T.-P. Loh, K.-T. Tan, Q.-Y. Hu, Angew. Chem., Int. Ed., 40, 2921 (2001); T.-P. Loh, C.-L. K. Lee, K.-T. Tan, Org. Lett., 4, 2985 (2002); K.-T. Tan, S.-S. Chng, H.-S. Cheng, T.-P. Loh, J. Am. Chem. Soc., 125, 2958 (2003)
26. T.-P. Loh, Q.-Y. Hu, L.-T. Ma, J. Am. Chem. Soc., 123, 2450 (2001); T.-P. Loh, K.-T. Tan, Q.-Y. Hu, Angew. Chem., Int. Ed., 40, 2921 (2001); T.-P. Loh, C.-L. K. Lee, K.-T. Tan, Org. Lett., 4, 2985 (2002); K.-T. Tan, S.-S. Chng, H.-S. Cheng, T.-P. Loh, J. Am. Chem. Soc., 125, 2958 (2003)
27. T.-P. Loh, Q.-Y. Hu, L.-T. Ma, J. Am. Chem. Soc., 123, 2450 (2001); T.-P. Loh, K.-T. Tan, Q.-Y. Hu, Angew. Chem., Int. Ed., 40, 2921 (2001); T.-P. Loh, C.-L. K. Lee, K.-T. Tan, Org. Lett., 4, 2985 (2002); K.-T. Tan, S.-S. Chng, H.-S. Cheng, T.-P. Loh, J. Am. Chem. Soc., 125, 2958 (2003)
28. T.-P. Loh, Q.-Y. Hu, L.-T. Ma, J. Am. Chem. Soc., 123, 2450 (2001); T.-P. Loh, K.-T. Tan, Q.-Y. Hu, Angew. Chem., Int. Ed., 40, 2921 (2001); T.-P. Loh, C.-L. K. Lee, K.-T. Tan, Org. Lett., 4, 2985 (2002); K.-T. Tan, S.-S. Chng, H.-S. Cheng, T.-P. Loh, J. Am. Chem. Soc., 125, 2958 (2003)