Anti-selective epoxidation of primary 5-(tert-butyl-dimethylsilyl)oxyallylic alcohols with m-chloro-peroxybenzoic acid

Heterocycles

Volumn 47, Issue 2, 1998, Pages 679-683

  Jørgensen, Kåre B ^a   Koshino, Hiroyuki ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001636147     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s(n)105     Document Type: Article

References (5)

1. T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5976;
2. T. Katsuki and V. S. Martin, 'Organic Reactions,' Vol. 48, ed. by L. A. Paquette, P. Beak, E. Ciganek, D. Curran, A. W. Czarnik, S. E. Denmark, L. Hegedus, R. C. Kelly, L. E. Overman, W. Roush, A. B. Smith, III, and J. D. White, John Wiley & Sons, Inc., New York, 1996, pp. 1-299.
3. The Sharpless AE of the 5,7-isopropylidene acetals of (5R,7S)- and (5R,7R)-dihydroxy-9-phenyl-2-nonen-1-ol using (+)-DET produced a mixture of anti- and syn-epoxides with low stereoselectivity (anti:syn=2.5:1 and 4.5:1, respectively).
4. M. Isobe, M. Kitamura, S. Mio, and T. Goto, Tetrahedron Lett., 1982, 23, 221;
5. M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 1984, 49, 3517.