Homologation of boronic esters with (dialkoxymethyl)lithiums. Asymmetric synthesis of α-alkoxy boronic esters

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5403-5408

  Carmès, Laurence ^a,b   Carreaux, François ^a   Carboni, Bertrand ^a  

^a Chimie et Photonique Moleculaires Rennes   (France)

^b King's Buildings ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; NOTE; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 0034714568     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000457r     Document Type: Note

References (74)

1. For a review of serine protease inhibitor, see: Hiratake, J.; Oda, J. Biosci. Biotech. Biochem. 1997, 61, 211-218. Threonine protease inhibitor: Adams, J.; Behnke, M.; Chen, S.; Cruickshank, A. A.; Dick, L. R.; Grenier, L.; Klunder, J. M.; Ma, Y.-T.; Plamondon, L.; Stein, R. L. Bioorg. Med. Chem. Lett. 1998, 8, 333-338.
2. For a review of serine protease inhibitor, see: Hiratake, J.; Oda, J. Biosci. Biotech. Biochem. 1997, 61, 211-218. Threonine protease inhibitor: Adams, J.; Behnke, M.; Chen, S.; Cruickshank, A. A.; Dick, L. R.; Grenier, L.; Klunder, J. M.; Ma, Y.-T.; Plamondon, L.; Stein, R. L. Bioorg. Med. Chem. Lett. 1998, 8, 333-338.
3. Brown, H. C.; Imai, T.; Desai, M. C.; Singaram, B. J. Am. Chem. Soc. 1985, 107, 4980-4983.
4. Carm̀es, L.; Carreaux, F.; Carboni, B.; Mortier, J. Tetrahedron Lett. 1998, 39, 555-556.
5. (a) Hoffmann, R. W.; Dresely, S. Chem. Ber. 1989, 122, 903-909.
6. (b) Hoffmann, R. W.; Wolff, J. J. Chem. Ber. 1991, 124, 563-569.
7. Andersen, M. W.; Hildebrandt, B.; Dahmann, G.; Hoffmann, R. W. Chem. Ber. 1991, 124, 2127-2139.
8. Matteson, D. S. J. Organomet. Chem. 1999, 581, 51-65.
9. (a) Matteson, D. S.; Sadhu, K. J. Am. Chem. Soc. 1983, 105, 2077-2078.
10. (b) Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819.
11. (c) Tripathy, P. B.; Matteson, D. S. Synthesis 1990, 200-206.
12. (d) Matteson, D. S.; Man, H.-W. J. Org. Chem. 1993, 58, 6545-6547.
13. (e) Matteson, D. S.; Man, H.-W.; Ho, O. C. J. Am. Chem. Soc. 1996, 118, 4560-4566.
14. (a) Matteson, D. S.; Peterson, M. L. J. Org. Chem. 1987, 52, 5116-5121.
15. (b) Matteson, D. S.; Kandil, A. A.; Soundararajan, R. J. Am. Chem. Soc. 1990, 112, 3964-3969.
16. (a) From α-alkoxyorganostannanes: ref 2.
17. (b) By homologation of boronic esters: Brown, H. C.; Imai, T. J. Am. Chem. Soc. 1983, 105, 6285-6289.
18. (c) From (1-methoxyvinyl)lithium: Matteson, D. S.; Beedle, E. C. Heteroatom Chem. 1990, 1, 135-140.
19. (d) From (α-alkoxy allyl)-lithium: Moret, E.; Schlosser, M. Tetrahedron Lett. 1984, 25, 4491-4494.
20. (a) Matteson, D. S.; Majumdar, D. J. Am. Chem. Soc. 1980, 102, 7590-7591.
21. (b) Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 1529-1535.
22. (c) Matteson, D. S.; Kandil, A. A. J. Org. Chem. 1987, 52, 5121-5124.
23. (d) Matteson, D. S.; Soundararajan, R.; Ho, O. C.; Gatzweiler, W. Organometallics 1996, 15, 152-163.
24. (a) Matteson, D. S.; Ray, R. J. Am. Chem. Soc. 1980, 102, 7590-7591.
25. (b) Matteson, D. S.; Ray, R.; Rocks, R. R.; Tsai, D. J. Organometallics 1983, 2, 1536-1543.
26. Rangaishenvi, M. V.; Singaram, B.; Brown, H. C. J. Org. Chem. 1991, 56, 3286-3294.
27. Matteson, D. S.; Erdik, E. Organometallics 1983, 2, 1083-1088.
28. Hoffmann, R. W.; Dresely, S. Tetrahedron Lett. 1987, 28, 5303-5306.
29. (a) Matteson, D. S. Stereodirected Synthesis with organoboranes; Springer: Berlin, 1995.
30. (b) Vaultier, M; Carboni, B. In Comprehensive Organometallic Chemistry II; Stone, F. G. A., Abel, E. V., Eds.; Pergamon: Oxford, 1995; Vol. 11, pp 191-276.
31. [Chloro(trimethylsilyl)methyl]lithium: (a) Matteson, D. S.; Majumdar, D. J. Organomet. Chem. 1980, 184, C41-C43.
32. (b) Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
33. (c) Tsai, D. J. S.; Matteson, D. S. Organometallics 1983, 2, 236-241. [Methoxy-(phenylthio)methyl]lithium: Reference 9b.
34. (Chloromethyl)lithium: (a) Sadhu, K. M.; Matteson, D. S. Organometallics 1985, 4, 1687-1689.
35. (b) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150-3155. (Bromomethyl)lithium: Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632. (Iodomethyl)lithium: Wallace, R. H.; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941-6944.
36. (b) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150-3155. (Bromomethyl)lithium: Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632. (Iodomethyl)lithium: Wallace, R. H.; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941-6944.
37. (b) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150-3155. (Bromomethyl)lithium: Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632. (Iodomethyl)lithium: Wallace, R. H.; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941-6944.
38. For a comparative study of different (halomethyl)lithiums, see: (a) Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8957-8960.
39. (b) Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8961-8964. (1,1-Dichloroethyl)lithium: Matteson, D. S.; Hurst, G. D. Heteroatom Chem. 1990, 1, 65-74. [(Chloroaryl)-methyl]lithium: Kabalka, G. W.; Li, N.-S.; Yu, S. Tetrahedron: Asymmetry 1997, 8, 3843-3846.
40. (b) Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8961-8964. (1,1-Dichloroethyl)lithium: Matteson, D. S.; Hurst, G. D. Heteroatom Chem. 1990, 1, 65-74. [(Chloroaryl)-methyl]lithium: Kabalka, G. W.; Li, N.-S.; Yu, S. Tetrahedron: Asymmetry 1997, 8, 3843-3846.
41. (b) Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8961-8964. (1,1-Dichloroethyl)lithium: Matteson, D. S.; Hurst, G. D. Heteroatom Chem. 1990, 1, 65-74. [(Chloroaryl)-methyl]lithium: Kabalka, G. W.; Li, N.-S.; Yu, S. Tetrahedron: Asymmetry 1997, 8, 3843-3846.
42. For reviews, see: (a) Matteson. D. S. Tetrahedron 1998, 54, 10555-10607.
43. (b) Reference 14a, Chapter 5.
44. (c) Brown, H. C.; Ramachaudran, P. V. Pure Appl. Chem. 1994, 66, 201-212.
45. (d) Matteson, D. S. Pure Appl. Chem. 1991, 63, 339-344.
46. (e) Matteson, D. S. Chem. Rev. 1989, 89, 1535-1551.
47. Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043-1054.
48. Shiner, C. S.; Tsunoda, T.; Goodman, B. A.; Ingham, S.; Lee, S.-H.; Vorndam, P. E. J. Am. Chem. Soc. 1989, 111, 1381-1392.
49. Duchêne, A.; Boissière, S.; Parrain, J. L.; Quintard, J.-P. J. Organomet. Chem. 1990, 387, 153-162.
50. (a) Midland, M. M; Zopola, A. R.; Halterman, R. L. J. Am. Chem. Soc. 1979, 101, 248-249.
51. (b) Matteson, D. S. Acc. Chem. Res. 1970, 3, 186-193.
52. (a) Quintard, J.-P.; Elissondo, B.; Pereyre, M. J. Organomet. Chem. 1981, 212, C31-C34.
53. (b) Quintard, J.-P.; Elissondo, B.; Mouko-Mpegna, D. J. Organomet. Chem. 1983, 257, 175-187.
54. Parrain, J. L.; Beaudet, I.; Cintrat, J. C.; Duchène, A.; Quintard, J.-P. Bull. Soc. Chim. Fr. 1994, 131, 304-312.
55. The Chemical Abstracts name for (+)-or (S)-pinanediol is [1S-(1α,2β,3β,5α)]-2,6,6-trimethylbicyclo[3.1.1]heptane-2, 3-diol.
56. The same chemical shift was observed when 4a was treated with lithium ethoxide in THF.
57. The same NMR study was realized with the (+)-pinanediol methylboronate 1g. The migration of the methyl group was observed at an upper temperature to -60°C.
58. -1. Dean, J. A. Ed. Lange's Handbook of Chemistry, Thirteenth Edition; MacGraw-Hill: New York, 1985; pp 3-128.
59. Matteson, D. S.; Sadhu, K. M. J. Am. Chem. Soc. 1983, 105, 2077-2078.
60. An excess of zinc chloride is also required during the Matteson homologation with compounds containing oxygen functionality. Reference 8a.
61. A mixture of 4a, lithium ethoxide and zinc chloride in THF was stirred overnight at room temperature. No detectable epimerization is observed only a small degradation of the product (∼2%).
62. Systematic names of 4: 4a, {3aS-[2(R*),3aα,4β,6β,7aα]}-2-[1-(ethoxy) phenylmethyl]hexahydro-3a,5,5-trimethyl-4-6-methano-1,3,2-benzodioxaborole; 4b, {3aS-[2(R*),3aα,4β,6β,7aα]}-2-[1-(ethoxy)(4- bromophenyl)methyl]hexahydro-3a,5,5-trimethyl-4-6-methano-1,3,2- benzodioxaborole; 4c, {3aS-[2(R*),3aα,4β,6β,7aα]}-2-[1-(ethoxy)(1- naphthyl)methyl]hexahydro-3a,5,5-trimethyl-4-6-methano-1,3,2-benzodioxaborole; 4e, {3aS-[2(R*),3aα,4β,6β,7aα]}-2-[1-(ethoxy)-2- methylethyl]hexahydro-3a,5,5-trimethyl-4-6-methano-1,3,2-benzodioxaborole; 4f, {3aS-[2(R*),3aα,4β,6β,7aα]}-2-[1-(ethoxy)-heptyl] hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole; 4g, {3aS-[2(R*),3aα,4β,6β,7aα]}-2-[1-(ethoxy)ethyl] hexahydro-3a,5,5-trimethyl-4-6-methano-1,3,2-benzodioxaborole; 4h, {3aS-[2(R*),3aα,4β,6β,7aα]}-2-[1-(methoxy) phenylmethyl]hexahydro-3a,5,5-trimethyl-4-6-methano-1,3,2-benzodioxaborole; 4i, {3aS-[2(R*),3aα,4β,6β,7aα]}-2-[1-(methoxy)ethyl] hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole. The 3aS designates the absolute configuration of the entire molecule by reference to carbon 3a. The 2(R*) indicates that this is the enantiomer in which the side chain at position 2 would have the R configuration if position 3a were R, but since position 3a is S, the side chain is S.
63. 7a with lithium ethoxide.
64. The α-ethoxy derivative 4d was obtained from the (+)-pinanediol 1-hexenylboronate without Lewis acid in 14% de, yield 50%.
65. No quantitative study of migratory aptitudes was carried out in homologation reaction, contrary to the oxidative deboronation. However, certain brief replies are given in the ref 15a.
66. Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1970, 9, 763-773.
67. Tsai, D. J. S.; Jesthi, P. K.; Matteson, D. S. Organometallics 1983, 2, 1543-1545.
68. (a) Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron: Asymmetry 1997, 8, 3711-3713.
69. (b) Midland, M. J. Org. Chem. 1998, 63, 914-915.
70. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165-168.
71. Brown, H. C.; Srebnik, M.; Cole, T. E. Organometallics 1986, 5, 2300-2303.
72. Brown, H. C.; Ravindran, N.; Kulkarni, S. U. J. Org, Chem. 1980, 45, 384-389.
73. Brown, H. C.; Campbell, J. B. J. Org. Chem. 1980, 45, 389-395.
74. Matteson, D. S.; Jesthi, P. K.; Sadhu, K. M. Organometallics 1984, 3, 1284-1288.