Alkyl carbonates: Efficient three component coupling of aliphatic alcohols, CO2, and alkyl halides in the presence of Cs2CO3

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4578-4579

  Kim, Seok In ^a   Chu, Feixia ^a   Dueno, Eric E ^a   Jung, Kyung Woon ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKYL GROUP; BROMIDE; CARBON DIOXIDE; CARBONIC ACID; CESIUM; HALIDE;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; ENVIRONMENTAL TEMPERATURE;

EID: 0033603624     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990520g     Document Type: Article

References (63)

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21. For alcoholysis of phosgene or its derivatives, see: (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894. (b) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395. (c) Keohan, F. L.; Freelin, R. G.; Riffle, J. S.; Yilgör, I.; McGrath, J. E. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 679. For organic carbonate exchange, see: (d) Grynkiewicz, G.; Jurczak, J.; Zamojski, A. Tetrahedron 1975, 31, 1411. (e) Shaikh, A.-A. G.; Sivaram, S. Ind. Eng. Chem. Res. 1998, 31, 1167. (f) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem. 1998, 63, 6031. For inorganic carbonate alkylation, see: (g) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122. (h) Bosworth, N.; Magnus, P.; Moore, R. J. Chem. Soc., Perkin Trans. 1 1973, 2694. (i) Lissel, M.; Dehmlow, E. V. Chem. Ber. 1981, 114, 1210.
22. For alcoholysis of phosgene or its derivatives, see: (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894. (b) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395. (c) Keohan, F. L.; Freelin, R. G.; Riffle, J. S.; Yilgör, I.; McGrath, J. E. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 679. For organic carbonate exchange, see: (d) Grynkiewicz, G.; Jurczak, J.; Zamojski, A. Tetrahedron 1975, 31, 1411. (e) Shaikh, A.-A. G.; Sivaram, S. Ind. Eng. Chem. Res. 1998, 31, 1167. (f) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem. 1998, 63, 6031. For inorganic carbonate alkylation, see: (g) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122. (h) Bosworth, N.; Magnus, P.; Moore, R. J. Chem. Soc., Perkin Trans. 1 1973, 2694. (i) Lissel, M.; Dehmlow, E. V. Chem. Ber. 1981, 114, 1210.
23. For alcoholysis of phosgene or its derivatives, see: (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894. (b) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395. (c) Keohan, F. L.; Freelin, R. G.; Riffle, J. S.; Yilgör, I.; McGrath, J. E. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 679. For organic carbonate exchange, see: (d) Grynkiewicz, G.; Jurczak, J.; Zamojski, A. Tetrahedron 1975, 31, 1411. (e) Shaikh, A.-A. G.; Sivaram, S. Ind. Eng. Chem. Res. 1998, 31, 1167. (f) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem. 1998, 63, 6031. For inorganic carbonate alkylation, see: (g) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122. (h) Bosworth, N.; Magnus, P.; Moore, R. J. Chem. Soc., Perkin Trans. 1 1973, 2694. (i) Lissel, M.; Dehmlow, E. V. Chem. Ber. 1981, 114, 1210.
24. For alcoholysis of phosgene or its derivatives, see: (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894. (b) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395. (c) Keohan, F. L.; Freelin, R. G.; Riffle, J. S.; Yilgör, I.; McGrath, J. E. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 679. For organic carbonate exchange, see: (d) Grynkiewicz, G.; Jurczak, J.; Zamojski, A. Tetrahedron 1975, 31, 1411. (e) Shaikh, A.-A. G.; Sivaram, S. Ind. Eng. Chem. Res. 1998, 31, 1167. (f) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem. 1998, 63, 6031. For inorganic carbonate alkylation, see: (g) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122. (h) Bosworth, N.; Magnus, P.; Moore, R. J. Chem. Soc., Perkin Trans. 1 1973, 2694. (i) Lissel, M.; Dehmlow, E. V. Chem. Ber. 1981, 114, 1210.
25. For alcoholysis of phosgene or its derivatives, see: (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894. (b) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395. (c) Keohan, F. L.; Freelin, R. G.; Riffle, J. S.; Yilgör, I.; McGrath, J. E. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 679. For organic carbonate exchange, see: (d) Grynkiewicz, G.; Jurczak, J.; Zamojski, A. Tetrahedron 1975, 31, 1411. (e) Shaikh, A.-A. G.; Sivaram, S. Ind. Eng. Chem. Res. 1998, 31, 1167. (f) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem. 1998, 63, 6031. For inorganic carbonate alkylation, see: (g) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122. (h) Bosworth, N.; Magnus, P.; Moore, R. J. Chem. Soc., Perkin Trans. 1 1973, 2694. (i) Lissel, M.; Dehmlow, E. V. Chem. Ber. 1981, 114, 1210.
26. For alcoholysis of phosgene or its derivatives, see: (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894. (b) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395. (c) Keohan, F. L.; Freelin, R. G.; Riffle, J. S.; Yilgör, I.; McGrath, J. E. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 679. For organic carbonate exchange, see: (d) Grynkiewicz, G.; Jurczak, J.; Zamojski, A. Tetrahedron 1975, 31, 1411. (e) Shaikh, A.-A. G.; Sivaram, S. Ind. Eng. Chem. Res. 1998, 31, 1167. (f) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem. 1998, 63, 6031. For inorganic carbonate alkylation, see: (g) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122. (h) Bosworth, N.; Magnus, P.; Moore, R. J. Chem. Soc., Perkin Trans. 1 1973, 2694. (i) Lissel, M.; Dehmlow, E. V. Chem. Ber. 1981, 114, 1210.
27. For alcoholysis of phosgene or its derivatives, see: (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894. (b) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395. (c) Keohan, F. L.; Freelin, R. G.; Riffle, J. S.; Yilgör, I.; McGrath, J. E. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 679. For organic carbonate exchange, see: (d) Grynkiewicz, G.; Jurczak, J.; Zamojski, A. Tetrahedron 1975, 31, 1411. (e) Shaikh, A.-A. G.; Sivaram, S. Ind. Eng. Chem. Res. 1998, 31, 1167. (f) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem. 1998, 63, 6031. For inorganic carbonate alkylation, see: (g) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122. (h) Bosworth, N.; Magnus, P.; Moore, R. J. Chem. Soc., Perkin Trans. 1 1973, 2694. (i) Lissel, M.; Dehmlow, E. V. Chem. Ber. 1981, 114, 1210.
28. For alcoholysis of phosgene or its derivatives, see: (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894. (b) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395. (c) Keohan, F. L.; Freelin, R. G.; Riffle, J. S.; Yilgör, I.; McGrath, J. E. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 679. For organic carbonate exchange, see: (d) Grynkiewicz, G.; Jurczak, J.; Zamojski, A. Tetrahedron 1975, 31, 1411. (e) Shaikh, A.-A. G.; Sivaram, S. Ind. Eng. Chem. Res. 1998, 31, 1167. (f) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem. 1998, 63, 6031. For inorganic carbonate alkylation, see: (g) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122. (h) Bosworth, N.; Magnus, P.; Moore, R. J. Chem. Soc., Perkin Trans. 1 1973, 2694. (i) Lissel, M.; Dehmlow, E. V. Chem. Ber. 1981, 114, 1210.
29. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
30. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
31. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
32. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
33. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
34. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
35. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
36. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
37. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
38. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
39. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
40. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
41. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
42. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
43. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
44. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
45. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
46. Carbon dioxide has been an attractive reagent because it is environmentally safe and economically inexpensive. For some examples of using carbon dioxide in carbonate formation, see: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205. (b) Kuran, W.; Pasynkiewicz, S.; Skupinska, J. Makromol. Chem. 1977, 178, 47. (c) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 431. (d) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626. (e) Frevel, L. K. U.S. Pat. 3,657,310, 1972. (f) Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1976, 415. (g) Inoue, S.; Koinuma, H.; Tsuruta, T. Polym. Lett. 1969, 7, 287. (h) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465. (i) Fang, S.; Fujimoto, K. Appl. Catal. A: Gen. 1996, 142, L1-L3. (j) Hori, Y.; Nahano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, H. Chem. Express 1986, 1, 224. (k) Carlo, V.; Rino, D. Span Pat. 479,522, 1980. (l) Kao, J.-L.; Wheaton, G. A.; Shalit, H.; Sheng, M. N. U.S. Pat. 4,247,465, 1981. (m) McGhee, W. D.; Talley, J. J. U.S. Pat. 5,302,717, 1994. (n) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Chem. Soc. Jpn. 1993, 985. (o) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi, L.; Moracci, F. M. Tetrahedron 1997, 53, 167. (p) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095. (q) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J. D.; Reibenapies, J. H. J. Am. Chem. Soc. 1998, 120, 4690. (r) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018.
47. For our cesium promoted O-alkylations, see: (a) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843. (b) Chu, F.; Dueno, E. E.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1847.
48. For our cesium promoted O-alkylations, see: (a) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843. (b) Chu, F.; Dueno, E. E.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1847.
49. Galli, C. Org. Prep. Proced. Int. 1992, 24, 287, and references therein.
50. Under basic conditions, α-hydroxy esters and lactones racemize easily, so alkylations of such moieties are usually carried out under acidic conditions. So far, silver catalyzed alkylations seem to be the most popular alkylation method, which is a costly process. (a) McKenzie, A.; Wren, H. J. Chem. Soc. 1919, 115, 602. (b) Bonner, W. A. J. Am. Chem. Soc. 1951, 73, 3126.
51. Under basic conditions, α-hydroxy esters and lactones racemize easily, so alkylations of such moieties are usually carried out under acidic conditions. So far, silver catalyzed alkylations seem to be the most popular alkylation method, which is a costly process. (a) McKenzie, A.; Wren, H. J. Chem. Soc. 1919, 115, 602. (b) Bonner, W. A. J. Am. Chem. Soc. 1951, 73, 3126.
52. The resulting carbonates were converted to the starting alcohols by hydrogenolysis, and the optical rotations of the produced products were compared with the values of the starting materials as well as those reported. Using (R)-methoxvphenylacetic acid, the corresponding esters were prepared from the decarbonylated alcohols, and the optical purities were measured by their proton NMR analysis.
53. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
54. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
55. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
56. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
57. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
58. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
59. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
60. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
61. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
62. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.
63. For selective examples, see: (a) Sheehan, J. C.; Guziec, F. S., Jr. J. Am. Chem. Soc. 1972, 94, 6561. (b) Satyanarayana, G.; Sivaram, S. Synth. Commun. 1990, 20, 3273. (c) Shute, R. E.; Rich, D. H. Synthesis 1987, 346. (d) Ghosh, A. K.; McKee, S. P.; Duong, T. T.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 1308. (e) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267. (f) Paquet, A. Can. J. Chem. 1982, 60, 976. (g) Bruneau, C.; Darcel, C.; Dixneuf, P. H. Curr. Org. Chem. 1997, 1, 197. (h) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332. (i) Greenberg, M. M.; Matray, T. J.; Kahl, J. D.; Yoo, D. J.; McMinn, D. L. J. Org. Chem. 1998, 63, 4062. (j) Kim, S.; Chang, H. J. Chem. Soc., Chem. Commun. 1983, 1357. (k) Renga, J. M. U.S. Pat. 4,612,386, 1986.