Diastereomerically pure 1,2-diols by nucleophilic displacement reactions of 3-oxetanols - A study directed towards the identification of suitable nucleophiles and the elucidation of possible side reactions

European Journal of Organic Chemistry

Volumn , Issue 10, 1998, Pages 2161-2169

  Bach, Thorsten ^a   Eilers, Frank ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

1,2 Diols; Alkyldealkoxylation; Oxetanes; Photocycloaddition; Ring opening

Indexed keywords

EID: 0004680937     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199810)1998:10<2161::AID-EJOC2161>3.0.CO;2-L     Document Type: Article

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30. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
31. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
32. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
33. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
34. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
35. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
36. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
37. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
38. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
39. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
40. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
41. Organolithium reagents: [14a] S. Searles, J. Am. Chem. Soc 1951, 73, 124-125. [14b] J. F. Ansell, B. Gadsby, J. Chem Soc 1958, 3388-3397. [14c] L. L. Darko, J. G. Cannon, J. Org. Chem. 1967, 32, 2352-2354. [14d] D. Hoppe, Angew. Chem. 1974, 86, 878-893; Angew. Chem. Int. Ed. Engl. 1974, 13, 789-803. [14e] N. J. Foulger, B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1 1974, 871-875. [14f] D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237. [14g] P. F. Hudrlik, C.-N. Wan, J Org. Chem. 1975, 40, 2963-2965. [14h] A. Maercker, M. Passlack, Chem. Ber. 1983, 116, 710-723. [14i] A. Maercker, R. Stötzel, Chem. Ber. 1987, 120, 1695-1706. [14j] C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham. S.-h. Lee, P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. [14k] R. Grigg, F. Heaney, J. Markandu. S. Surendrakumar, M. Thornton-Pett, W. J. Warnock, Tetrahedron 1991, 47, 4007-4030. [14l] J. Fuchs, G. Szeimies, Chem. Ber. 1992, 125, 2517-2522.
42. Organomagnesium reagents: [15a] C. G. Derrick, D. W. Bissell, J. Am. Chem. Soc. 1916, 38, 2478-2486. [15b] W. Steudel, H. Gilman, J. Am. Chem. Soc. 1960, 82, 6129-6132. [15c] F. B. Slezak, J. P. Stallings, D. H. Wagner, J. H. Wotiz, J Org. Chem. 1961, 26, 3137-3140. [15d] L. R. Kray, M. G. Reinecke, J. Org. Chem. 1967, 32, 225-227. [15e] E. N. Marvell, D. Sturmer, R. S. Knutson, J. Org. Chem. 1968, 33, 2991-2993. [15f] R. D. Ricke, M. S. Sell, H. Xiong, J. Org. Chem. 1995, 60, 5143-5149.
43. Organomagnesium reagents: [15a] C. G. Derrick, D. W. Bissell, J. Am. Chem. Soc. 1916, 38, 2478-2486. [15b] W. Steudel, H. Gilman, J. Am. Chem. Soc. 1960, 82, 6129-6132. [15c] F. B. Slezak, J. P. Stallings, D. H. Wagner, J. H. Wotiz, J Org. Chem. 1961, 26, 3137-3140. [15d] L. R. Kray, M. G. Reinecke, J. Org. Chem. 1967, 32, 225-227. [15e] E. N. Marvell, D. Sturmer, R. S. Knutson, J. Org. Chem. 1968, 33, 2991-2993. [15f] R. D. Ricke, M. S. Sell, H. Xiong, J. Org. Chem. 1995, 60, 5143-5149.
44. Organomagnesium reagents: [15a] C. G. Derrick, D. W. Bissell, J. Am. Chem. Soc. 1916, 38, 2478-2486. [15b] W. Steudel, H. Gilman, J. Am. Chem. Soc. 1960, 82, 6129-6132. [15c] F. B. Slezak, J. P. Stallings, D. H. Wagner, J. H. Wotiz, J Org. Chem. 1961, 26, 3137-3140. [15d] L. R. Kray, M. G. Reinecke, J. Org. Chem. 1967, 32, 225-227. [15e] E. N. Marvell, D. Sturmer, R. S. Knutson, J. Org. Chem. 1968, 33, 2991-2993. [15f] R. D. Ricke, M. S. Sell, H. Xiong, J. Org. Chem. 1995, 60, 5143-5149.
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