Enantioselective addition of organometallics to aldehydes using camphor derived chiral 1,4-aminoalcohols as ligands

Tetrahedron Asymmetry

Volumn 10, Issue 20, 1999, Pages 3969-3975

  Knollmüller, Max ^a   Ferencic, Mathias ^a   Gärtner, Peter ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AMINOALCOHOL; BENZALDEHYDE; BROMINE DERIVATIVE; CAMPHOR; DIETHYLZINC; HEXANE; LIGAND; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; ORGANOMETALLIC COMPOUND;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0038054855     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00413-9     Document Type: Article

References (37)

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14. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
15. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
16. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
17. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
18. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
19. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
20. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
21. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
22. Selected papers about the enantioselective addition reaction of organolithium compounds: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585. (c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. (d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegass, K.; Hirsch, K. A.; Bollinger, A. M.; Grosz, A. L.; Mani, V. Tetrahedron 1994, 50, 6109. (f) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590. (g) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. (h) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028. (i) Corruble A.; Valnot J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
23. Selected papers about the enantioselective addition reaction of Grignard compounds: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (c) Weber, B.; Seebach, D. Angew. Chem. 1992, 104, 96; Angew. Chem., Int. Ed. Engl. 1992, 31, 84.
24. Selected papers about the enantioselective addition reaction of Grignard compounds: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (c) Weber, B.; Seebach, D. Angew. Chem. 1992, 104, 96; Angew. Chem., Int. Ed. Engl. 1992, 31, 84.
25. Selected papers about the enantioselective addition reaction of Grignard compounds: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (c) Weber, B.; Seebach, D. Angew. Chem. 1992, 104, 96; Angew. Chem., Int. Ed. Engl. 1992, 31, 84.
26. Selected papers about the enantioselective addition reaction of Grignard compounds: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (c) Weber, B.; Seebach, D. Angew. Chem. 1992, 104, 96; Angew. Chem., Int. Ed. Engl. 1992, 31, 84.
27. Schön, M.; Naef, R. Tetrahedron: Asymmetry 1999, 10, 169.
28. Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117.
29. Knollmüller, M.; Gärtner, P.; Letschnig, M. Monatsh. Chem. 1998, 129, 953.
30. For reviews, see: (a) Ref. 3; (b) Ref. 4; (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994; Chapter 5.
31. Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489.
32. Cho, B. T.; Kim, N. J. Chem. Soc., Perkin Trans. 1 1996, 2901.
33. Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264.
34. Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
35. Nugent, W. A. Chem. Commun. 1999, 1369.
36. Noe, C. R.; Knollmüller, M.; Gärtner, P.; Mereiter, K.; Steinbauer, G. Liebigs Ann. 1996, 1015.
37. For an excellent review, see: Evans, D. A. Science (Washington, DC) 1988, 240, 420.