Tandem aminoxylation-allylation reactions: A rapid, asymmetric conversion of aldehydes to mono-substituted 1,2-diols

Chemical Communications

Volumn 4, Issue 5, 2004, Pages 606-607

  Zhong, Guofu ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE;

ALLYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 1642380424     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b314356b     Document Type: Article

References (33)

1. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless: Chem. Rev., 1994 94:2483.
2. S. Y. Ko, A. W. M. Lee, S. Masamune, L. A. Reed III, K. B. Sharpless, F. J. Walker: Tetrahedron, 1990 46:245.
3. S. Y. Ko, A. W. M. Lee, S. Masamune, L. A. Reed III, K. B. Sharpless, F. J. Walker: Tetrahedron, 1990 46:245.
4. H. J. M. Gijsen, L. Qiao, W. Fitz, C.-H. Wong: Chem. Rev., 1996 96:443.
5. M. D. Bednarski, E. S. Simon, N. Bischofberger, W.-D. Fessner, M.-J. Kim, W. Lees, T. Saito, H. Waldmann, G. M. Whitesides: J. Am. Chem. Soc., 1989 111:627.
6. W.-D. Fessner, G. Sinerius, A. Schneider, M. Dreyer, G. E. Schulz, J. Badia, J. Aguilar: Angew. Chem., Int. Ed. Engl., 1991 30:555.
7. 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.
8. 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.
9. G. Zhong, D. Shabat, B. List, J. Anderson, S. C. Sinha, R. A. Lerner, C. F. Barbas III: Angew. Chem., Int. Ed., 1998 37:2481.
10. H. Hanessian: Total Synthesis of Natural Products: the ‘Chiron’ Approach, Pergamon Press, Oxford, 1983.
11. J. Seyden-Penne: in Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley-Interscience, New York, 1995.
12. E. N. Jacobsen, I. Markó, W. S. Mungall, G. Schröder, K. B. Sharpless: J. Am. Chem. Soc., 1988 110:1968.
13. L. Wang, K. B. Sharpless: J. Am. Chem. Soc., 1992 114:7568.
14. W. Notz, B. List: J. Am. Chem. Soc., 2000 122:7386.
15. N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Ohshima, T. Suzuki, M. Shibasaki: J. Am. Chem. Soc., 2001 123:2466.
16. B. M. Trost, H. Ito, E. R. Silcoff: J. Am. Chem. Soc., 2001 123:3367.
17. G. Zhong: Angew. Chem., Int. Ed., 2003 42:4247.
18. A. Cordova, W. Notz, C. F. Barbas III: J. Org. Chem., 2002 67:301.
19. A. Northrup, D. W. C. MacMillan: J. Am. Chem. Soc., 2002 124:6798.
20. A. Cordova, S.-I. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III: J. Am. Chem. Soc., 2002 124:1866.
21. A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen: Angew. Chem., Int. Ed., 2002 41:1790.
22. B. List: J. Am. Chem. Soc., 2002 124:5656.
23. D. Enders: in Asymmetric Synthesis Vol. 3 (Ed.: J. D. Morrison), Academic Press, Orlando, 1984, p. 275.
24. D. Enders, P. Fey, H. Kipphardt: Org. Synth., 1987 65:173 and 183.
25. A. Job, C. F. Janeck, W. Bettray, R. Peters, D. Enders: Tetrahedron, 2002 58:2253.
26. L. A. Paquette, T. M. Mitzel: J. Am. Chem. Soc., 1996 118:1931.
27. L. A. Paquette: Synthesis, 2003 765.
28. C.-J. Li: Chem. Rev., 1993 93:2023.
29. A. Lubineau, J. Augé, Y. Queneau: Synlett, 1995 1087.
30. C.-J. Li: Tetrahedron, 1996 52:5643.
31. L. A. Paquette: in Green Chemistry: Recent Advances in Chemical Processing, ACS Symposium Series, Vol. 767; ACS, Washington DC, 2000, p. 100.
32. N. Momiyama, H. Yamamoto: J. Am. Chem. Soc., 2003 125:6038.
33. N. Momiyama, H. Yamamoto: Angew. Chem., Int. Ed., 2002 41:2986.