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2005
Carbohydrates
U 0500
Elimination Reactions of Glycosyl Selenoxides. — Various 1,2-trans-selenoglycoare converted by a Sharpless-type oxidation into 1,2-trans glycosyl selenoxides.
01- 174 sides
The latter undergo spontaneous in situ syn elimination to yield the corresponding protected 2-hydroxy and 2-amino glycals in high yields. The method is advantageous to
the alternative sulfoxide approach: neither isolation of intermediate oxidation products
nor elevated temperatures are required. However, this method is not applicable to substrates bearing unprotected hydroxyl groups. — (CHAMBERS, D. J.; EVANS, G. R.;
FAIRBANKS*, A. J.; Tetrahedron 60 (2004) 38, 8411-8419; Chem. Res. Lab., Univ.
Oxford, Oxford OX1 3TA, UK; Eng.) — Klein
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