A Grignard-Type Addition of Allyl Unit to Carbonyl Compounds Containing a Carboxyl Group by Using BiCl3-Zn(0)-Allyl Bromide

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 9, 1997, Pages 2265-2267

  Wada, Makoto ^a   Honna, Munckazu ^a   Kuramoto, Yoshihiro ^a   Miyoshi, Norikazu ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000563076     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.2265     Document Type: Article

References (41)

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7. Reviews on organic reactions in aqueous media: a) R. Pardo and M. Santelli, Bull. Chem. Soc. Fr., 1985, 99; b) C. Einhorn, J. Einhorn, and J.-L. Luche, Synthesis, 1989, 787; c) H.-U. Ressig, in "Organic Synthesis Highlights," VCH, Weinheim (1991), p. 71; d) C.-J. Li, Chem. Rev., 93, 2023 (1993); e) S. Kobayashi, I. Hachiya, and T. Takahori, Synthesis, 1993, 371; f) A. Lubineau, J. Auge, and Y. Queneau, Synthesis, 1994, 741; g) C.-J. Li, Tetrahedron, 52, 5643 (1996).
8. Reviews on organic reactions in aqueous media: a) R. Pardo and M. Santelli, Bull. Chem. Soc. Fr., 1985, 99; b) C. Einhorn, J. Einhorn, and J.-L. Luche, Synthesis, 1989, 787; c) H.-U. Ressig, in "Organic Synthesis Highlights," VCH, Weinheim (1991), p. 71; d) C.-J. Li, Chem. Rev., 93, 2023 (1993); e) S. Kobayashi, I. Hachiya, and T. Takahori, Synthesis, 1993, 371; f) A. Lubineau, J. Auge, and Y. Queneau, Synthesis, 1994, 741; g) C.-J. Li, Tetrahedron, 52, 5643 (1996).
9. Reviews on organic reactions in aqueous media: a) R. Pardo and M. Santelli, Bull. Chem. Soc. Fr., 1985, 99; b) C. Einhorn, J. Einhorn, and J.-L. Luche, Synthesis, 1989, 787; c) H.-U. Ressig, in "Organic Synthesis Highlights," VCH, Weinheim (1991), p. 71; d) C.-J. Li, Chem. Rev., 93, 2023 (1993); e) S. Kobayashi, I. Hachiya, and T. Takahori, Synthesis, 1993, 371; f) A. Lubineau, J. Auge, and Y. Queneau, Synthesis, 1994, 741; g) C.-J. Li, Tetrahedron, 52, 5643 (1996).
10. Reviews on organic reactions in aqueous media: a) R. Pardo and M. Santelli, Bull. Chem. Soc. Fr., 1985, 99; b) C. Einhorn, J. Einhorn, and J.-L. Luche, Synthesis, 1989, 787; c) H.-U. Ressig, in "Organic Synthesis Highlights," VCH, Weinheim (1991), p. 71; d) C.-J. Li, Chem. Rev., 93, 2023 (1993); e) S. Kobayashi, I. Hachiya, and T. Takahori, Synthesis, 1993, 371; f) A. Lubineau, J. Auge, and Y. Queneau, Synthesis, 1994, 741; g) C.-J. Li, Tetrahedron, 52, 5643 (1996).
11. Reviews on organic reactions in aqueous media: a) R. Pardo and M. Santelli, Bull. Chem. Soc. Fr., 1985, 99; b) C. Einhorn, J. Einhorn, and J.-L. Luche, Synthesis, 1989, 787; c) H.-U. Ressig, in "Organic Synthesis Highlights," VCH, Weinheim (1991), p. 71; d) C.-J. Li, Chem. Rev., 93, 2023 (1993); e) S. Kobayashi, I. Hachiya, and T. Takahori, Synthesis, 1993, 371; f) A. Lubineau, J. Auge, and Y. Queneau, Synthesis, 1994, 741; g) C.-J. Li, Tetrahedron, 52, 5643 (1996).
12. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
13. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
14. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
15. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
16. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
17. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
18. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
19. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
20. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
21. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
22. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
23. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
24. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
25. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
26. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
27. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
28. The allylation reactions of carbonyl compounds using allylic halides and Zn, Sn, or In in aqueous media were previously reported. a) C. Petrier and J.-L. Luche, J. Org. Chem., 50, 910 (1985); b) C. Peterier, J.-L. Luche, J. Einhorn, and J. Luche, Tetrahedron Lett., 26, 1449 (1985); c) J. Einhorn and J.-L. Luche, J. Organomet. Chem., 322, 177 (1987); d) H. Mattes and C. Benezra, Tetrahedron Lett., 26, 5697 (1985); e) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 54, 3087 (1989); f) J. Nokami, J. Otera, T. Sudo, and R. Okawara, Organometallics, 2, 191 (1983); g) K. Uneyama, N. Kamaki, A. Moriya, and S. Torii, J. Org. Chem., 50, 5396 (1985); h) K. Uneyama, H. Nambu, and S. Torii, Tetrahedron Lett., 27, 2395 (1986); i) S. Wu, B. Huang, and X. Gao, Synth.Commun., 20, 1279 (1990); j) W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); k) J. Gao, R. Harter, D. M. Gordon, and G. M. Whitesides, J. Org. Chem., 59, 3714 (1994); l) E. Kim, D. M. Gordon, W. Schimd, and G. M. Whitesides, J. Org. Chem., 58, 5500 (1993); m) C.-J. Li and T.-H. Chan, Tetrahedron Lett., 32, 7017 (1991); n) Y. Oda, S. Matsuo, and K. Saito, Tetrahedron Lett., 33, 97 (1992); o) T.-H. Chan and C.-J. Li, J. Chem. Soc., Chem. Commun., 1992, 747; p) C.-J. Li and Y.-Q. Lu, Tetrahedron Lett., 36, 2721 (1995); q) M. B. Isaac and T.-H. Chan, Tetrahedron Lett., 36, 957 (1995).
29. a) M. Wada and K. Akiba, Tetrahedron Lett., 26, 4211 (1985);
30. b) M. Wada, H. Ohki, and K. Akiba, Tetrahedron Lett., 27, 4771 (1986);
31. c) M. Wada, H. Ohki, and K. Akiba, J. Chem. Soc., Chem. Commun., 1987, 708;
32. d) M. Wada, H. Ohki, and K. Akiba, Bull. Chem. Soc. Jpn., 63, 1738 (1990).
33. a) Only one example of allylation of the carbonyl compound containing a carboxyl group by allyl bromide and metallic tin in the presence of water has been reported using 4-oxopentanoic acid in which the yield of allylation was low.
34. 2-Amberlyst 15: P. Talaga, M. Schaeffer, C. Benezra, and J.-L. Stamp, Synthesis, 1990, 530; using In: a) T.-H. Chan and M.-C. Lee, J. Org. Chem., 60, 4228 (1995); b) T.-P. Loh and X.-R. Li, Chem. Commun., 1996, 1929; c) T.-P. Loh, D. S.-C. Ho, K.-C. Xu, and K.-Y. Sim, Tetrahedron Lett., 38, 865 (1996); d) T.-P. Loh and X.-R. Li, Tetrahedron Lett., 38, 869 (1996).
35. 2-Amberlyst 15: P. Talaga, M. Schaeffer, C. Benezra, and J.-L. Stamp, Synthesis, 1990, 530; using In: a) T.-H. Chan and M.-C. Lee, J. Org. Chem., 60, 4228 (1995); b) T.-P. Loh and X.-R. Li, Chem. Commun., 1996, 1929; c) T.-P. Loh, D. S.-C. Ho, K.-C. Xu, and K.-Y. Sim, Tetrahedron Lett., 38, 865 (1996); d) T.-P. Loh and X.-R. Li, Tetrahedron Lett., 38, 869 (1996).
36. 2-Amberlyst 15: P. Talaga, M. Schaeffer, C. Benezra, and J.-L. Stamp, Synthesis, 1990, 530; using In: a) T.-H. Chan and M.-C. Lee, J. Org. Chem., 60, 4228 (1995); b) T.-P. Loh and X.-R. Li, Chem. Commun., 1996, 1929; c) T.-P. Loh, D. S.-C. Ho, K.-C. Xu, and K.-Y. Sim, Tetrahedron Lett., 38, 865 (1996); d) T.-P. Loh and X.-R. Li, Tetrahedron Lett., 38, 869 (1996).
37. 2-Amberlyst 15: P. Talaga, M. Schaeffer, C. Benezra, and J.-L. Stamp, Synthesis, 1990, 530; using In: a) T.-H. Chan and M.-C. Lee, J. Org. Chem., 60, 4228 (1995); b) T.-P. Loh and X.-R. Li, Chem. Commun., 1996, 1929; c) T.-P. Loh, D. S.-C. Ho, K.-C. Xu, and K.-Y. Sim, Tetrahedron Lett., 38, 865 (1996); d) T.-P. Loh and X.-R. Li, Tetrahedron Lett., 38, 869 (1996).
38. 2-Amberlyst 15: P. Talaga, M. Schaeffer, C. Benezra, and J.-L. Stamp, Synthesis, 1990, 530; using In: a) T.-H. Chan and M.-C. Lee, J. Org. Chem., 60, 4228 (1995); b) T.-P. Loh and X.-R. Li, Chem. Commun., 1996, 1929; c) T.-P. Loh, D. S.-C. Ho, K.-C. Xu, and K.-Y. Sim, Tetrahedron Lett., 38, 865 (1996); d) T.-P. Loh and X.-R. Li, Tetrahedron Lett., 38, 869 (1996).
39. 2-Amberlyst 15: P. Talaga, M. Schaeffer, C. Benezra, and J.-L. Stamp, Synthesis, 1990, 530; using In: a) T.-H. Chan and M.-C. Lee, J. Org. Chem., 60, 4228 (1995); b) T.-P. Loh and X.-R. Li, Chem. Commun., 1996, 1929; c) T.-P. Loh, D. S.-C. Ho, K.-C. Xu, and K.-Y. Sim, Tetrahedron Lett., 38, 865 (1996); d) T.-P. Loh and X.-R. Li, Tetrahedron Lett., 38, 869 (1996).
40. 3-Al(0). See Ref. 4d.
41. 3-Zn(0) even if benzoic acid was present in the reaction mixture, and benzoic acid was recovered intact. See Ref. 4d.