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2005
Pyran derivatives
R 0340
Regio- and Enantioselective Synthesis of Novel Functionalized Pyranopyrroby 1,3-Dipolar Cycloaddition of Carbohydrates. — This potentially widely
32- 134 lidines
adaptable methodology for the synthesis of pyranopyrrolidines (VIII) and (X) utilizes
a highly selective [3 + 2] cycloaddition reaction of azomethine ylides with the chiral
carbohydrate-derived enone (VI) as the major feature. The strictly regio- and stereoselective reaction gives rise to single enantiomeric compounds in all cases. The method
is atom-economical with no loss of chiral inducing fragments and amenable to diversity
since the choice of functionality on the starting material determines the substitution pattern present in the products. — (BASHIARDES*, G.; CANO, C.; MAUZE, B.;
Synlett 2005, 4, 587-590; Dep. Chim., Methodol. Synth. Biomol., Univ. Poitiers,
F-86022 Poitiers, Fr.; Eng.) — H. Hoennerscheid
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