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2005
Carbohydrates
U 0500
Synthesis of C-Glycosyl Amino Acids: Scope and Limitations of the Tandem
Approach. — Esters derived from glycals (I) or (VII) and a variety of
24- 178 Tebbe/Claisen
amino acids are synthesized to study the title approach. Limitations are found for
O-tert-butyl-protected aspartic acid derivatives (Ve) and (VIII), which give only poor
yields of the corresponding methylenated products. Esters derived from substituted
α-amino acids do not react. For glutamic acid derivative (XI), a satisfactory yield of
methylene compound (XII) is obtained. The final thermal rearrangement proceeds
smoothly under conditions C). — (CHAMBERS, D. J.; EVANS, G. R.;
FAIRBANKS*, A. J.; Tetrahedron: Asymmetry 16 (2005) 1, 45-55; Chem. Res. Lab.,
Univ. Oxford, Oxford OX1 3TA, UK; Eng.) — Klein
2005
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