Tetrahedron: Asymmetry

Aldehyde–alkene cyclizations via O-stannyl ketyl radicals using sugars as chiral auxiliaries

EJ Enholm, F Allais, S Bareyt

文献索引：Enholm, Eric J.; Allais, Florent; Bareyt, Sebastian Tetrahedron Asymmetry, 2003 , vol. 14, # 19 p. 2871 - 2874

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被引用次数: 10

摘要

This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for aldehyde–alkene radical cyclizations. Diastereomeric ratios as high as 9: 1 were achieved with an ester-appended (+)-isosorbide and 100: 1 for (+)- isomannide. Temperature dependence, Lewis acids and solvents were all examined.