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200517.fm Page 218 Friday, March 18, 2005 2:52 PM
2005
Carbohydrates
U 0500
Hg(II) Reagent-Controlled Stereoselective Synthesis of 2,5-cis- and
Pyrrolidines. — The stereoselectivity of intramolecular
17- 198 2,5-trans-Polyhydroxylated
amidomercuration of δ-alkenylcarbamates (I) and (IV) is shown to depend on the protection state and stereochemistry at the position α to the vinyl group as well as on the
nature of mercury salt and reaction temperature. Thus, 2,5-cis-selectivity is observed
for the first time in the amidomercuration of δ-alkenylcarbamate (I) using mercuric trifluoroacetate at -78 °C. In contrast, 2,5-trans-selectivity is observed for the diastereomer (IV) irrespective of the reaction conditions tested. — (CHIKKANNA, D.; HAN*,
H.; Synlett 2004, 13, 2311-2314; Dep. Chem., Univ. Tex., San Antonio,
TX 78249, USA; Eng.) — Mischke
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