Building Blocks for the Stereocontrolled Synthesis of 1,3-Diols of Various Configurations

Synlett

Volumn 1997, Issue 2, 1997, Pages 225-228

  Weigand, Stefan ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002774473     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-732     Document Type: Article

References (57)

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12. 5 (starting from compound 3), respectively.
13. The dissolving metal reduction of acetonides which contain an alkyl and a C = N group at the carbon atom which bears the PhS group and a hydrogen atom in compound 2 also leads to syn-1,3-diol acetonides: Rychnovsky, S. D.; Zeller, S.; Skalitzky, D. J.; Griesgraber, G. J. Org. Chem. 1990, 55, 5550-5551.
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17. 2: S. L. Schreiber, M. T. Goulet, J. Am. Chem. Soc. 1987, 109, 8120-8122 (footnote 13). (b) Enolate of (2-hydroxy-1,2,2-triphenylethyl(acetate: Mahler, U.; Devant, R. M.; Braun, M.; Chem. Ber. 1988, 121, 2035-2044; Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 635-668. (c) 2,5-Dimethylborolane enolate of (1,1-diethylpropylthio)acetate: Duplanlier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081. (d) 2-(α-Chloroallyl)-4,5-dicyclohexyl-1,3-dioxo-2-borolane: Hoffmann, R. W.; Stürmer, R.; Synlett 1990, 759-761. (e) Functionalized organozinc reagents: Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
18. 2: S. L. Schreiber, M. T. Goulet, J. Am. Chem. Soc. 1987, 109, 8120-8122 (footnote 13). (b) Enolate of (2-hydroxy-1,2,2-triphenylethyl(acetate: Mahler, U.; Devant, R. M.; Braun, M.; Chem. Ber. 1988, 121, 2035-2044; Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 635-668. (c) 2,5-Dimethylborolane enolate of (1,1-diethylpropylthio)acetate: Duplanlier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081. (d) 2-(α-Chloroallyl)-4,5-dicyclohexyl-1,3-dioxo-2-borolane: Hoffmann, R. W.; Stürmer, R.; Synlett 1990, 759-761. (e) Functionalized organozinc reagents: Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
19. 2: S. L. Schreiber, M. T. Goulet, J. Am. Chem. Soc. 1987, 109, 8120-8122 (footnote 13). (b) Enolate of (2-hydroxy-1,2,2-triphenylethyl(acetate: Mahler, U.; Devant, R. M.; Braun, M.; Chem. Ber. 1988, 121, 2035-2044; Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 635-668. (c) 2,5-Dimethylborolane enolate of (1,1-diethylpropylthio)acetate: Duplanlier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081. (d) 2-(α-Chloroallyl)-4,5-dicyclohexyl-1,3-dioxo-2-borolane: Hoffmann, R. W.; Stürmer, R.; Synlett 1990, 759-761. (e) Functionalized organozinc reagents: Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
20. 2: S. L. Schreiber, M. T. Goulet, J. Am. Chem. Soc. 1987, 109, 8120-8122 (footnote 13). (b) Enolate of (2-hydroxy-1,2,2-triphenylethyl(acetate: Mahler, U.; Devant, R. M.; Braun, M.; Chem. Ber. 1988, 121, 2035-2044; Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 635-668. (c) 2,5-Dimethylborolane enolate of (1,1-diethylpropylthio)acetate: Duplanlier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081. (d) 2-(α-Chloroallyl)-4,5-dicyclohexyl-1,3-dioxo-2-borolane: Hoffmann, R. W.; Stürmer, R.; Synlett 1990, 759-761. (e) Functionalized organozinc reagents: Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
21. 2: S. L. Schreiber, M. T. Goulet, J. Am. Chem. Soc. 1987, 109, 8120-8122 (footnote 13). (b) Enolate of (2-hydroxy-1,2,2-triphenylethyl(acetate: Mahler, U.; Devant, R. M.; Braun, M.; Chem. Ber. 1988, 121, 2035-2044; Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 635-668. (c) 2,5-Dimethylborolane enolate of (1,1-diethylpropylthio)acetate: Duplanlier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081. (d) 2-(α-Chloroallyl)-4,5-dicyclohexyl-1,3-dioxo-2-borolane: Hoffmann, R. W.; Stürmer, R.; Synlett 1990, 759-761. (e) Functionalized organozinc reagents: Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
22. 2: S. L. Schreiber, M. T. Goulet, J. Am. Chem. Soc. 1987, 109, 8120-8122 (footnote 13). (b) Enolate of (2-hydroxy-1,2,2-triphenylethyl(acetate: Mahler, U.; Devant, R. M.; Braun, M.; Chem. Ber. 1988, 121, 2035-2044; Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 635-668. (c) 2,5-Dimethylborolane enolate of (1,1-diethylpropylthio)acetate: Duplanlier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079-7081. (d) 2-(α-Chloroallyl)-4,5-dicyclohexyl-1,3-dioxo-2-borolane: Hoffmann, R. W.; Stürmer, R.; Synlett 1990, 759-761. (e) Functionalized organozinc reagents: Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
23. (a) Ley, S. V.; Anthony, N. J.; Armstrong, A.; Brasca, M. G.; Clarke, T.; Culshaw, D.; Greck, C.; Grice, P.; Jones, A. B.; Lygo, B.; Madin, A.; Sheppard, R. N.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1989, 45, 7161-7194.
24. (b) Rychnovsky, S. D.; Griesgraber, G.; Zeller, S.; Skalitzky, D. J. J. Org. Chem. 1991, 56, 5161-5169.
25. Lipshutz, B. H.; Moretti, R.; Crow, R. Tetrahedron Lett. 1989, 30, 15-18.
26. Lespieau, R.; Bourguel, M. Org. Synth., Coll. Vol. 1 (Gilman, H.; Blat, A. H., Eds.), 2nd ed., John Wiley&Sons, New York, pp. 209-211.
27. 3), IR spectra (film), and - with the exception of compound 24 - combustion analyses.
28. de Meijere, A. Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
29. de Meijere, A. Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
30. Voigt, K.; Lansky, A.; Noltemeyer, M.; de Meijere, A. Liebigs Ann. 1996, 899-911.
31. (a) Wershofen, S.; Scharf, H.-D. Synthesis 1988, 854-858 (>91% ee).
32. (b) Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212-7214 (84% ee, 88% ee).
33. (c) Narjes, F.; Schaumann, E. Liebigs Ann. 1993, 841-846 (85% ee).
34. (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
35. (b) K. B. Sharpless in I. Ojima, "Catalytic Asymmetric Synthesis", VCH, Weinheim 1993, 227-272.
36. (c) Pfenninger, A. Synthesis 1986, 89-116.
37. The ee of epoxyalcohol 12 was determined by gas chromatography on an enantiomerically pure stationary phase containing heptakis(2,6-di-O-methyl-3-O-pentyl)-β-cyclodextrin. The racemic epoxyalcohol 12 (synthesized for comparison purposes by the method of Mihelich, E. D.; Daniels, K.; Eickhoff, D. I. J. Am. Chem. Soc. 1981, 103, 7690-7692) exhibited two baseline-separated peaks of equal height. The enantio-enriched sample of 12 caused a major GLC peak which coincided with the more slowly emerging enantiomer of racemic 12 and a minor peak which had the same retention time as the more rapidly emerging enantiomer of racemic 12.
38. Aoyama, Y.; Urabe, H.; Sato, F. Tetrahedron Lett. 1991, 32, 6731-6734. This paper entails the first application of the procedure developed for the dictation-controlled reduction of α-chiral α,β-epoxy ketones by Nakata, T.; Tanaka, T.; Oishi, T Tetrahedron Lett. 1981, 22, 4723-4726 to a trans-configurated α,β-epoxy ketone.
39. Aoyama, Y.; Urabe, H.; Sato, F. Tetrahedron Lett. 1991, 32, 6731-6734. This paper entails the first application of the procedure developed for the dictation-controlled reduction of α-chiral α,β-epoxy ketones by Nakata, T.; Tanaka, T.; Oishi, T Tetrahedron Lett. 1981, 22, 4723-4726 to a trans-configurated α,β-epoxy ketone.
40. Fujii, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 967-970.
41. Nakata, T.; Suenaga, T.; Nakashima, K.; Oishi, T. Tetrahedron Lett. 1989, 30, 6529-6532.
42. (a) Menges, M.; Brückner, R. Synlett 1994, 809-813.
43. (b) Menges, M.; Brückner, R. Liebigs. Ann. 1995, 365-384.
44. 4Si (462.7): C 72.69, H 7.41; found: C 72.82. H 7.42.
45. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986-997. - Alternative regioselective reductions of epoxyalcohols (Kirshenbaum, K. S.; Sharpless, K. B. Chem. Lett. 1987, 11-14; Page, B. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc. Perkin Trans. I 1990, 2403-2408; Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596-2599) worked less satisfactory in our hands.
46. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986-997. - Alternative regioselective reductions of epoxyalcohols (Kirshenbaum, K. S.; Sharpless, K. B. Chem. Lett. 1987, 11-14; Page, B. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc. Perkin Trans. I 1990, 2403-2408; Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596-2599) worked less satisfactory in our hands.
47. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986-997. - Alternative regioselective reductions of epoxyalcohols (Kirshenbaum, K. S.; Sharpless, K. B. Chem. Lett. 1987, 11-14; Page, B. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc. Perkin Trans. I 1990, 2403-2408; Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596-2599) worked less satisfactory in our hands.
48. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986-997. - Alternative regioselective reductions of epoxyalcohols (Kirshenbaum, K. S.; Sharpless, K. B. Chem. Lett. 1987, 11-14; Page, B. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc. Perkin Trans. I 1990, 2403-2408; Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596-2599) worked less satisfactory in our hands.
49. We are indebted to Dr. Andreas Gansäuer (Universität Göttingen) for suggesting this method.
50. 4Si (462.7): C 72.69, H 7.41; found: C 72.36, H 7.18.
51. 22b and the data in footnote 19 of Menges, M.; Brückner, R. Synlett 1993, 901-905.- (b) Priepke, H; Brückner, R. manuscript in preparation for Liebigs Ann.; Allerheiligen, S.; Brückner, R. manuscript in preparation for Liebigs Ann.
52. 22b and the data in footnote 19 of Menges, M.; Brückner, R. Synlett 1993, 901-905.- (b) Priepke, H; Brückner, R. manuscript in preparation for Liebigs Ann.; Allerheiligen, S.; Brückner, R. manuscript in preparation for Liebigs Ann.
53. 22b and the data in footnote 19 of Menges, M.; Brückner, R. Synlett 1993, 901-905.- (b) Priepke, H; Brückner, R. manuscript in preparation for Liebigs Ann.; Allerheiligen, S.; Brückner, R. manuscript in preparation for Liebigs Ann.
54. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945-948; Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515.
55. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945-948; Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515.
56. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099-7100.
57. Previous use of this method: Hoffmann, R.; Brückner R. Chem. Ber. 1992, 125, 1471-1484.