Enantioselective synthesis of O-methoxycarbonyl cyanohydrins: Chiral building blocks generated by bifunctional catalysis with BINOLAM-AlCl

European Journal of Organic Chemistry

Volumn , Issue 8, 2006, Pages 1949-1958

  Baeza, Alejandro ^a   Casas, Jesús ^a   Nájera, Carmen ^a   Sansano, José M ^a   Saá, José M ^b  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSITAT DE LES ILLES BALEARS   (Spain)

Author keywords

Aluminium; Asymmetric synthesis; Bifunctional catalysis; BINOLAM; Cyanohydrin derivatives

Indexed keywords

EID: 33646198861     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500939     Document Type: Article

References (68)

1. For recent reviews, see: a) M. North, Synlett 1993, 807-820;
2. b) F. Effenberger, Angew. Chem. Int. Ed. Engl. 1994, 33, 1555-1563;
3. c) R. J. H. Gregory, Chem. Rev. 1999, 99, 3649-3682;
4. d) M. North, Tetrahedron: Asymmetry 2003, 14, 147-176;
5. e) Synthesis and Applications of Non-Racemic Cyanohydrins and a-Amino Acids. Tetrahedron Symposium in Print (Ed.: M. North), 2004, 60, 10371-10568;
6. f) M. North, Science of Synthesis (Ed.: S.-I. Murahashi), vol. 19, pp. 235-284, Thieme, Stuttgart, 2004;
7. g) J.-M. Brunel, I. P. Holmes, Angew. Chem. Int. Ed. 2004, 43, 2752-2778;
8. h) P. Poechlauer, W. Skranc, M. Wubbolts, Asymmetric Catalysis on Industrial Scale. (Eds.: H. U. Blaser, E. Schmidt). Wiley-VCH, Weinheim, 2004, pp. 151-164.
9. For the preparation of racemic O-acylcyanohydrins see: a) H. M. R. Hoffmann, Z. M. Ismail, R. Hollweg, A. R. Zein, Bull. Chem. Soc., Jpn. 1990, 63, 1807-1810;
10. b) M. Scholl, C.-K. Lim, G. C. Fu, J. Org. Chem. 1995, 60, 6229-6231;
11. c) M. Okimoto, T. Chiba, Synthesis 1996, 1188-1190;
12. d) A. Baeza, C. Nájera, M. G. Retamosa, J. M. Sansano, Synthesis 2005, 2787-2797.
13. For the preparation of racemic cyanohydrin-O-phosphates see: a) I. Micó, C. Nájera, Tetrahedron 1993, 49, 4327-4332 and references cited therein;
14. b) A. Baeza, C. Nájera, J. M. Sansano, Arkivoc 2005, ix, 353-363.
15. a) A. T. Au, Synth. Commun. 1984, 14, 743-748;
16. b) D.-S. Shin, Y.-S. Jung, J.-J. Kim, C. Ahn, Bull. Korean Chem. Soc. 1998, 19, 119-120;
17. c) D. Berthiaume, D. Poirier, Tetrahedron 2000, 56, 5995-6003;
18. d) D. R. Deardorff, C. M. Taniguchi, S. A. Tafti, H. Y. Kim, S. Y. Choi, K. J. Downey, T. V. Nguyen, J. Org. Chem. 2001, 66, 7191-7194;
19. e) X. Linghu, D. A. Nicewicz, J. S. Johnson, Org. Lett. 2002, 4, 2957-2960;
20. f) N. Thanasa, V. Prachywarakorn, S. Tontoolarug, S. Ruchirawat, Tetrahedron Lett. 2003, 44, 1019-1021.
21. S.-K. Tian, L. Deng, J. Am. Chem. Soc. 2001, 123, 6195-6196.
22. a) J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. Int. Ed. 2002, 41, 3636-3638;
23. b) J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Org. Lett. 2003, 5, 3021-3024.
24. a) Y. N. Belokon', A. J. Blacker, L. A. Clutterbuck, M. North, Org. Lett. 2003, 5, 4505-4507;
25. b) S. Lundgren, E. Wingstrand, M. Penhoat, C. Moberg, J. Am. Chem. Soc. 2005, 127, 11592-11593.
26. For reviews about bifunctional catalysis see: a) H. Gröger, Chem. Eur. J. 2001, 7, 5246-5251;
27. b) G. J. Rowlands, Tetrahedron 2001, 57, 1865-1882;
28. c) M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1189-1199;
29. d) S. Matsunaga, T. Ohshima, M. Shibasaki, Adv. Synth. Catal. 2002, 344, 3-15;
30. e) M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491-1508.
31. a) J. Casas, C. Nájera, J. M. Saá, J. M. Sansano, Org. Lett. 2002, 4, 2589-2592;
32. b) J. Casas, C. Nájera, J. M. Saá, J. M. Sansano, Tetrahedron Symposium in Print 2004, 60, 10487-10496.
33. For the firstly reported preparation of enantiomerically enriched cyanohydrin O-phosphates, see: a) A. Baeza, J. Casas, C. Nájera, J. M. Sansano, J. M. Saá, Angew. Chem. Int. Ed. 2003, 42, 3143-3146;
34. b) A. Baeza, C. Nájera, J. M. Sansano, J. M. Saá, Chem. Eur. J. 2005, 11, 3849-3862.
35. A. Baeza, C. Nájera, J. M. Sansano, J. M. Saá, Tetrahedron: Asymmetry 2005, 16, 2385-2389.
36. For a preliminary communication see: J. Casas, A. Baeza, J. M. Sansano, C. Nájera, J. M. Saá, Tetrahedron: Asymmetry 2003, 14, 197-200.
37. For synthetic applications of (S)- and (R)-BINOLAM 5, see: a) As suitable phase-transfer catalysts for the enantioselective alkylation of the aldimine Schiff bases of alanine esters, see: J. Casas, C. Nájera, J. M. Sansano, J. González, J. M. Saá, M. Vega, Tetrahedron: Asymmetry 2001, 12, 699-702;
38. b) In the addition of diethylzinc to aldehydes, see: H. Kitajima, K. Iti, T. Katsuki, Chem. Lett. 1996, 343-344;
39. c) In the enantioselective Simmons-Smith cyclopropanation, see: H. Kitajima, K. Ito, T. Katsuki, Chem. Lett. 1995, 1113-1114;
40. d) In the enantioselective Michael additions, see: H. Kitajima, K. Ito, T. Katsuki, Tetrahedron 1997, 53, 17015-17028.
41. E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. Int. Ed. 1999, 38, 1570-1577.
42. Thermogravimetric analysis revealed that 4-Å mol. sieves dried at 120°C for 4 h contained 7.5% of water.
43. J. A. Joule, K. Mills, G. F. Smith, Heterocyclic Chemistry, 3rd ed., Chapman & Hall, London, 1995, p. 371.
44. a) D. Sawada, M. Shibasaki, Angew. Chem. Int. Ed. 2000, 39, 209-213;
45. b) D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 10521-10532;
46. c) Y. Hamashima, D. Sawada, H. Nogami, M. Kanai, M. Shibasaki, Tetrahedron 2001, 57, 805-814.
47. For some recent reviews of NLE see, for example: a) C. Girard, H. B. Kagan, Angew. Chem. Int. Ed. 1998, 37, 2922-2959;
48. b) D. R. Fenwick, H. B. Kagan, in: Topics in Stereochemistry (Ed.: S. E. Denmark), John Wiley & Sons, New York, 1999, vol. 22, pp. 257-296;
49. c) D. Heller, H.-J. Drexler, C. Fischer, H. Buschmann, W. Baumann, B. Heller, Angew. Chem. Int. Ed. 2000, 39, 495-499;
50. d) K. Soai, T. Shibata, I. Sato, Acc. Chem. Res. 2000, 33, 382-390;
51. e) H. B. Kagan, Synlett 2001, 888-899;
52. f) H. B. Kagan, Adv. Synth. Catal. 2001, 343, 227-233.
53. T. Aoi, K. Kagoshima, K. Maruoka, J. Am. Chem. Soc. 1997, 119, 5754-5755.
54. The X-ray structure of the pentacoordinate BINOL-AlMe-(THF) dimer complex has been described: T. Arai, H. Sasai, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 441-442.
55. D. A. Atwood, M. J. Harvey, Chem. Rev. 2001, 101, 37-52.
56. E. J. Corey, T. W. Lee, Chem. Commun. 2001, 1321-1329.
57. C. Duplais, F. Bures, I. Sapountzis, T. J. Korn, G. Cahiez, P. Knochel, Angew. Chem. Int. Ed. 2004, 43, 2968-2970.
58. M. K. Basu, F.-T. Luo, Tetrahedron Lett. 1998, 39, 3005-3006.
59. a) T. Nemoto, H. Kakei, V. Gnanadesikan, S. Tosaki, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2002, 124, 14544-14545;
60. b) J. M. Concellón, E. Bardales, Org. Lett. 2003, 5, 4783-4785.
61. A. M. Kawamoto, M. Aparecida, M. Wills, J. Chem. Com., Perkin Trans. 1 2001, 1916-1928.
62. S. Caddick, D. B. Judd, A. K. de K. Lewis, M. T. Reich, M. R. Williams, Tetrahedron 2003, 59, 5417-5423.
63. Commercially available from MEDALCHEMY S. L.
64. K. Iwakami, Y. Hinakubo, T. Oriyama, Tetrahedron Lett. 2005, 46, 5881-5883.
65. P. G. M. Wuts, S. W. Ashford, A. M. Anderson, J. R. Atkins, Org. Lett. 2003, 5, 1483-1485.
66. D. R. Deardorff, C. M. Taniguchi, A. C. Nelson, A. P. Pace, A. J. Kim, A. K. Pace, R. A. Jones, S. A. Tafti, C. Nguyen, C. O'Connor, J. Tang, J. Chen, Tetrahedron: Asymmetry 2005, 16, 1655-1661.
67. R. T. Buck, D. M. Coe, M. J. Drysdale, C. J. Moody, N. D. Pearson, Tetrahedron Lett. 1998, 39, 7181-7184.
68. Dictionary of Organic Compounds, Chapman and Hall, New York, 1982, 5th ed., vol. 3, p. 3270.