A facile and rapid route to highly enantiopure 1,2-diols by novel catalytic asymmetric α-aminoxylation of aldehydes

Angewandte Chemie - International Edition

Volumn 42, Issue 35, 2003, Pages 4247-4250

  Zhong, Guofu ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Alcohols; Aldehydes; Asymmetric catalysis; Enantioselectivity; Proline

Indexed keywords

ALDEHYDES; CATALYSIS; REDUCTION;

OXYGEN SOURCES;

ALCOHOLS;

1,2 DIOL DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE; OXYGEN; PROLINE; UNCLASSIFIED DRUG;

ALPHA AMINOXYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS;

EID: 0141522552     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352097     Document Type: Article

References (42)

1. a) H. Hanessian, Total Synthesis of Natural Products: the "Chiron" Approach, Pergamon, Oxford, 1983;
2. b) B. T. Cho, Y. S. Chun, J. Org. Chem. 1998, 63, 5280-5282;
3. c) B. T. Cho, Y. S. Chun, Tetrahedron: Asymmetry 1999, 10, 1843-1846.
4. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
5. For the enzymatic synthesis, see M. D. Burkart, Z. Zhang, S.-C. Hung, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 11743-11746.
6. a) D. Enders in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, Orlando, 1984, p. 275;
7. b) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173-178, 183-194;
8. c) D. Enders, V. Bhushan, Tetrahedron Lett. 1988, 29, 2437-2440;
9. d) A. Job, C. F. Janeck, W. Bettray, R. Peters, D. Enders, Tetrahedron 2002, 58, 2253-2329.
10. For antibody mimics, see a) J. Wagner, R. A. Lerner, C. F. Barbas III, Science 1995, 270, 1797-1800;
11. b) G. Zhong, T. Hoffmann, R. A. Lerner, S. Danishefsky, C. R. Barbas III, J. Am. Chem. Soc. 1997, 119, 8131-8132;
12. c) C. F. Barbas III, A. Heine, G. Zhong, T. Hoffmann, S. Gramatikova, R. Björnestedt, B. List, J. Anderson, E. A. Stura, E. A. Wilson, R. A. Lerner, Science 1997, 278, 2085-2092;
13. d) T. Hoffmann, G. Zhong, B. List, D. Shabat, J. Anderson, S. Gramatikova, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 1998, 120, 2768-2779;
14. f) G. Zhong, D. Shabat, B. List, J. Anderson, S. C. Sinha, R. A. Lerner, C. F. Barbas III, Angew. Chem. 1998, 110, 2609-2612; Angew. Chem. Int. Ed. 1998, 37, 2481-2484;
15. f) G. Zhong, D. Shabat, B. List, J. Anderson, S. C. Sinha, R. A. Lerner, C. F. Barbas III, Angew. Chem. 1998, 110, 2609-2612; Angew. Chem. Int. Ed. 1998, 37, 2481-2484;
16. g) G. Zhong, R. A. Lerner, C. F. Barbas III, Angew. Chem. 1999, 111, 3957-3960; Angew. Chem. Int. Ed. 1999, 38, 3738-3741.
17. g) G. Zhong, R. A. Lerner, C. F. Barbas III, Angew. Chem. 1999, 111, 3957-3960; Angew. Chem. Int. Ed. 1999, 38, 3738-3741.
18. a) A. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798-6799;
19. b) A. Cordova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303;
20. c) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621;
21. d) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493; Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
22. d) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493; Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
23. e) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267;
24. f) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396.
25. a) A. Cordova, S.-i. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867;
26. b) A. Cordova, W Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843;
27. c) B. List, P. Polarjiev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833.
28. a) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740;
29. b) A. Enders, A. Seki, Synlett 2002, 26-28.
30. K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536-1539; Angew. Chem. Int. Ed. 2003, 42, 1498-1501, and references therein.
31. K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536-1539; Angew. Chem. Int. Ed. 2003, 42, 1498-1501, and references therein.
32. a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793;
33. a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793;
34. b) B. List, J. Am. Chem. Soc. 2002, 124, 5656-5657;
35. c) N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bogevig, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 6254-6255.
36. For studies using natural class I aldolases in organic synthesis, see H. J. M. Gijsen, L. Qiao, W. Fitz, C.-H. Wong, Chem. Rev. 1996, 96, 443-473.
37. N. Momiyama, H. Yamamoto, Org. Lett. 2002, 4, 3579-3582.
38. a) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2003, 125, 6038-6039;
39. b) N. Momiyama, H. Yamamoto, Angew. Chem. 2002, 114, 3112-3114; Angew. Chem. Int. Ed. 2002, 41, 2986-2988.
40. b) N. Momiyama, H. Yamamoto, Angew. Chem. 2002, 114, 3112-3114; Angew. Chem. Int. Ed. 2002, 41, 2986-2988.
41. S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 11273-11283.
42. Nitroso compounds have been used to generate C-O bonds in Diel-Alder reactions, see P. F. Vogt, M. J. Miller, Tetrahedron 1998, 54, 1317-1348.