Catalysis

Enantioselective synthesis

Biology

Materials science

Enantiopure drug

Cleavage (geology)

Geology

Stereochemistry

Paleontology

Medicinal chemistry

Organic chemistry

Nucleophile

Series (stratigraphy)

Composite material

Fracture (geology)

Chemistry

Ring (chemistry)

Journal of the Chemical Society Perkin Transactions 1

The readily available gem-dibromocyclopropanes 5 and 6 undergo silver(I)-promoted electrocyclic ring-opening and the resulting π-allyl cations trapped with a range of nucleophiles to give mixtures of cyclohexenyl bromides such as 7–9 and 17–19, respectively. Subjection of certain of these products to ozonolytic cleavage followed by reduction protocols then affords differentially protected and enantiopure D- and L-series 3-deoxy- and 2-amino-2,3-dideoxyaldohexoses.

Ring-fused gem-dibromocyclopropanes as precursors to enantiomerically pure D- and L-series 3-deoxy- and 2-amino-2,3-dideoxyaldohexose derivatives