A systematic study of ligand effects on a lewis-acid-catalyzed Diels- Alder reaction in water. Water-enhanced enantioselectivity

Journal of the American Chemical Society

Volumn 121, Issue 29, 1999, Pages 6798-6806

  Otto, Sijbren ^a,b   Engberts, Jan B F N ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b LEHIGH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; COPPER; DIAMINE; LIGAND; NICKEL; POLYCYCLIC AROMATIC HYDROCARBON; WATER;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL REACTION; ENTHALPY; ENTROPY; EQUILIBRIUM CONSTANT; REACTION ANALYSIS; REACTION TIME;

EID: 0033612740     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984273u     Document Type: Article

References (99)

1. For reviews, see: (a) Tomioka, K. Synthesis 1990, 541. (b) Narasaka, K. Synthesis 1991, 1. (c) Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993. (d) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. For reviews, see: (a) Tomioka, K. Synthesis 1990, 541. (b) Narasaka, K. Synthesis 1991, 1. (c) Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993. (d) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. For reviews, see: (a) Tomioka, K. Synthesis 1990, 541. (b) Narasaka, K. Synthesis 1991, 1. (c) Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993. (d) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. For reviews, see: (a) Tomioka, K. Synthesis 1990, 541. (b) Narasaka, K. Synthesis 1991, 1. (c) Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993. (d) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
5. Only a few quantitative studies have been reported. See, for example: Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800.
6. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
7. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
8. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
9. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
10. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
11. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
12. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
13. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
14. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
15. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
16. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
17. This is illustrated by mechanistic studies of the effect of achiral ligands on decarboxylation [(a) Rund, J. V.; Plane, R. A. J. Am. Chem. Soc. 1964, 86, 367. (b) Hay, R. W.; Leong, K. N. J. Chem. Soc., Chem. Commun. 1967, 800. (c) Rund, J. V.; Claus, K. G. J. Am. Chem. Soc. 1967, 89, 2256. (d) Rund, J. V.; Claus, K. C. Inorg. Chem. 1968, 7, 860. (e) Claus, K. G.; Rund, J. V. Inorg. Chem. 1969, 8, 59. (f) Leong, K. N.; Lister, M. W. Can. J. Chem. 1971, 50, 1461. (g) Raghavan, N. V.; Leussing, D. L. J. Am. Chem. Soc. 1977, 99, 2188] and hydrolytic reactions [(h) Hay, R. W.; Morris, P. J. J. Chem. Soc. A 1971, 1524. (i) Angelici, R. J.; Allison, J. W. Inorg. Chem. 1971, 10, 2238. (j) Hay, R. W.; Morris, P. J. J. Chem. Soc., Dalton Trans. 1973, 56. (k) Nakon, R.; Rechani, P. R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 2117. (l) Schneider, H.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.].
18. For reviews, see: (a) Li, C. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A. Chem. Ind. 1996, 123. (c) Engberts, J. B. F. N.; Feringa, B. L.; Keller, E.; Otto, S. Recl. Trav. Chim. Pays-Bas 1996, 115, 457. (d) Cornils, B.; Herrmann, W. A.; Eckl, R. W. J. Mol. Catal., A Chem. 1997, 116, 27. (e) Li, C.; Chen, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997. (f) Organic Synthesis in Water, Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
19. For reviews, see: (a) Li, C. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A. Chem. Ind. 1996, 123. (c) Engberts, J. B. F. N.; Feringa, B. L.; Keller, E.; Otto, S. Recl. Trav. Chim. Pays-Bas 1996, 115, 457. (d) Cornils, B.; Herrmann, W. A.; Eckl, R. W. J. Mol. Catal., A Chem. 1997, 116, 27. (e) Li, C.; Chen, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997. (f) Organic Synthesis in Water, Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
20. For reviews, see: (a) Li, C. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A. Chem. Ind. 1996, 123. (c) Engberts, J. B. F. N.; Feringa, B. L.; Keller, E.; Otto, S. Recl. Trav. Chim. Pays-Bas 1996, 115, 457. (d) Cornils, B.; Herrmann, W. A.; Eckl, R. W. J. Mol. Catal., A Chem. 1997, 116, 27. (e) Li, C.; Chen, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997. (f) Organic Synthesis in Water, Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
21. For reviews, see: (a) Li, C. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A. Chem. Ind. 1996, 123. (c) Engberts, J. B. F. N.; Feringa, B. L.; Keller, E.; Otto, S. Recl. Trav. Chim. Pays-Bas 1996, 115, 457. (d) Cornils, B.; Herrmann, W. A.; Eckl, R. W. J. Mol. Catal., A Chem. 1997, 116, 27. (e) Li, C.; Chen, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997. (f) Organic Synthesis in Water, Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
22. For reviews, see: (a) Li, C. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A. Chem. Ind. 1996, 123. (c) Engberts, J. B. F. N.; Feringa, B. L.; Keller, E.; Otto, S. Recl. Trav. Chim. Pays-Bas 1996, 115, 457. (d) Cornils, B.; Herrmann, W. A.; Eckl, R. W. J. Mol. Catal., A Chem. 1997, 116, 27. (e) Li, C.; Chen, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997. (f) Organic Synthesis in Water, Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
23. For reviews, see: (a) Li, C. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A. Chem. Ind. 1996, 123. (c) Engberts, J. B. F. N.; Feringa, B. L.; Keller, E.; Otto, S. Recl. Trav. Chim. Pays-Bas 1996, 115, 457. (d) Cornils, B.; Herrmann, W. A.; Eckl, R. W. J. Mol. Catal., A Chem. 1997, 116, 27. (e) Li, C.; Chen, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997. (f) Organic Synthesis in Water, Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
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27. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakagushi, H. Synlett 1995, 975.
28. The beneficial influence of water on the Diels-Alder reaction has already been reported in 1973 (Eggelte, T. A.; de Koning, H.; Huisman, H. O. Tetrahedron 1973, 29, 2491 ) and has become generally recognized by the work of Breslow et al. (Rideout, D. C.; Breslow, R. J. J. Am. Chem. Soc. 1980, 102, 7816). For recent references, see: (a) Otto, S.; Blokzijl, W.; Engberts, J. B. F. N. J. Org. Chem. 1994, 59, 5372. (b) Engberts, J. B. F. N. Pure Appl. Chem. 1995, 67, 823, (c) Otto, S. Ph.D. Thesis, University of Groningen, 1998.
29. The beneficial influence of water on the Diels-Alder reaction has already been reported in 1973 (Eggelte, T. A.; de Koning, H.; Huisman, H. O. Tetrahedron 1973, 29, 2491 ) and has become generally recognized by the work of Breslow et al. (Rideout, D. C.; Breslow, R. J. J. Am. Chem. Soc. 1980, 102, 7816). For recent references, see: (a) Otto, S.; Blokzijl, W.; Engberts, J. B. F. N. J. Org. Chem. 1994, 59, 5372. (b) Engberts, J. B. F. N. Pure Appl. Chem. 1995, 67, 823, (c) Otto, S. Ph.D. Thesis, University of Groningen, 1998.
30. The beneficial influence of water on the Diels-Alder reaction has already been reported in 1973 (Eggelte, T. A.; de Koning, H.; Huisman, H. O. Tetrahedron 1973, 29, 2491 ) and has become generally recognized by the work of Breslow et al. (Rideout, D. C.; Breslow, R. J. J. Am. Chem. Soc. 1980, 102, 7816). For recent references, see: (a) Otto, S.; Blokzijl, W.; Engberts, J. B. F. N. J. Org. Chem. 1994, 59, 5372. (b) Engberts, J. B. F. N. Pure Appl. Chem. 1995, 67, 823, (c) Otto, S. Ph.D. Thesis, University of Groningen, 1998.
31. The beneficial influence of water on the Diels-Alder reaction has already been reported in 1973 (Eggelte, T. A.; de Koning, H.; Huisman, H. O. Tetrahedron 1973, 29, 2491 ) and has become generally recognized by the work of Breslow et al. (Rideout, D. C.; Breslow, R. J. J. Am. Chem. Soc. 1980, 102, 7816). For recent references, see: (a) Otto, S.; Blokzijl, W.; Engberts, J. B. F. N. J. Org. Chem. 1994, 59, 5372. (b) Engberts, J. B. F. N. Pure Appl. Chem. 1995, 67, 823, (c) Otto, S. Ph.D. Thesis, University of Groningen, 1998.
32. The beneficial influence of water on the Diels-Alder reaction has already been reported in 1973 (Eggelte, T. A.; de Koning, H.; Huisman, H. O. Tetrahedron 1973, 29, 2491 ) and has become generally recognized by the work of Breslow et al. (Rideout, D. C.; Breslow, R. J. J. Am. Chem. Soc. 1980, 102, 7816). For recent references, see: (a) Otto, S.; Blokzijl, W.; Engberts, J. B. F. N. J. Org. Chem. 1994, 59, 5372. (b) Engberts, J. B. F. N. Pure Appl. Chem. 1995, 67, 823, (c) Otto, S. Ph.D. Thesis, University of Groningen, 1998.
33. (a) Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645.
34. (b) Quo, S.; Bertoncin, F.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1996, 118, 7702.
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38. (f) Zhu, Z.; Espenson, J. H. J. Am. Chem. Soc. 1997, 119, 3507. We failed to observe any catalytic effects of methylrhenium trioxide (ref 8f) and indium trichloride (ref 8c) on the rate of the model Diels-Alder reaction of methyl vinyl ketone with cyclopentadiene in aqueous solution under homogeneous conditions (for details, see ref 7c, pp 108-110).
39. We have recently demonstrated that micelles can even further increase the efficiency of a Lewis-acid-catalyzed Diels-Alder reaction: Otto, S.; Engberts, J. B. F. N.; Kwak, J. C. T. J. Am. Chem. Soc. 1998, 120, 9517.
40. Some examples have been reported. See ref 3d,e, and g. For a review on ligand-accelerated catalysis, see: Berrisford, D. J.; Bol, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.
41. Preliminary communication: Otto, S.; Boccaletti, G.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1998, 120, 4238.
42. 8b
43. Martell, A. E.; Hancock, R. D. Metal Complexes in Aqueous Solutions; Plenum Press: New York, 1996.
44. Martell, A. E. Stability Constants of Metal-Ion Complexes; Chemical Society: London, 1971.
45. a above the value for the nickel aqua ion. It is not unlikely that the methyl groups of the ligand hinder coordination of the water molecules in the two remaining equatorial positions of the complex, facilitating their displacement by the dienophile. (16) (a) Takasu, M.; Yamamoto, H. Synlett 1990, 194. (b) Sartor, D.; Saffrich, J.; Helmchen, G.; Richards, C. J.; Lambert, H. Tetrahedron: Asymmetry 1991, 2, 639. (c) Corey, E. J.; Loh, T. J. Am. Chem. Soc. 1991, 113, 8966. (d) Seerden, J.-P. G.; Scheeren, J. W. Tetrahedron Lett. 1993, 34, 2669. (e) Seerden, J.-P. G. Ph.D. Thesis, University of Nijmegen, 1995.
46. a above the value for the nickel aqua ion. It is not unlikely that the methyl groups of the ligand hinder coordination of the water molecules in the two remaining equatorial positions of the complex, facilitating their displacement by the dienophile. (16) (a) Takasu, M.; Yamamoto, H. Synlett 1990, 194. (b) Sartor, D.; Saffrich, J.; Helmchen, G.; Richards, C. J.; Lambert, H. Tetrahedron: Asymmetry 1991, 2, 639. (c) Corey, E. J.; Loh, T. J. Am. Chem. Soc. 1991, 113, 8966. (d) Seerden, J.-P. G.; Scheeren, J. W. Tetrahedron Lett. 1993, 34, 2669. (e) Seerden, J.-P. G. Ph.D. Thesis, University of Nijmegen, 1995.
47. a above the value for the nickel aqua ion. It is not unlikely that the methyl groups of the ligand hinder coordination of the water molecules in the two remaining equatorial positions of the complex, facilitating their displacement by the dienophile. (16) (a) Takasu, M.; Yamamoto, H. Synlett 1990, 194. (b) Sartor, D.; Saffrich, J.; Helmchen, G.; Richards, C. J.; Lambert, H. Tetrahedron: Asymmetry 1991, 2, 639. (c) Corey, E. J.; Loh, T. J. Am. Chem. Soc. 1991, 113, 8966. (d) Seerden, J.-P. G.; Scheeren, J. W. Tetrahedron Lett. 1993, 34, 2669. (e) Seerden, J.-P. G. Ph.D. Thesis, University of Nijmegen, 1995.
48. a above the value for the nickel aqua ion. It is not unlikely that the methyl groups of the ligand hinder coordination of the water molecules in the two remaining equatorial positions of the complex, facilitating their displacement by the dienophile. (16) (a) Takasu, M.; Yamamoto, H. Synlett 1990, 194. (b) Sartor, D.; Saffrich, J.; Helmchen, G.; Richards, C. J.; Lambert, H. Tetrahedron: Asymmetry 1991, 2, 639. (c) Corey, E. J.; Loh, T. J. Am. Chem. Soc. 1991, 113, 8966. (d) Seerden, J.-P. G.; Scheeren, J. W. Tetrahedron Lett. 1993, 34, 2669. (e) Seerden, J.-P. G. Ph.D. Thesis, University of Nijmegen, 1995.
49. a above the value for the nickel aqua ion. It is not unlikely that the methyl groups of the ligand hinder coordination of the water molecules in the two remaining equatorial positions of the complex, facilitating their displacement by the dienophile. (16) (a) Takasu, M.; Yamamoto, H. Synlett 1990, 194. (b) Sartor, D.; Saffrich, J.; Helmchen, G.; Richards, C. J.; Lambert, H. Tetrahedron: Asymmetry 1991, 2, 639. (c) Corey, E. J.; Loh, T. J. Am. Chem. Soc. 1991, 113, 8966. (d) Seerden, J.-P. G.; Scheeren, J. W. Tetrahedron Lett. 1993, 34, 2669. (e) Seerden, J.-P. G. Ph.D. Thesis, University of Nijmegen, 1995.
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51. The term "arène-arene interaction" is used to denote the noncovalent interactions between two aromatic systems, without specifying their nature.
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72. 3.
73. -1 in the presence of glycine.
74. See ref 2 and references therein.
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89. Some studies of solvent effects on the enantioselectivity of Diels-Alder reactions catalyzed by chiral Lewis acids have been published. The sometimes dramatic effects have been brought down to influences on ion pairing and the geometry of the dienophile-Lewis acid complex. See: (a) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079. (b) Johannsen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 2 1997, 1183.
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