Synthesis of Protected Aminocyclohexanediols

Spencer Knapp, Dinesh V. Patel

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24 Scopus citations


As the model study for the synthesis of aminocyclitols and amino sugars, 2-cyclohexen-1-ol (1) was converted to five of the seven possible (1, 2, 3)-aminocyclohexanediols in protected form (4a, 6a, 11a, 13a, and 18a). Two flexible new approaches were employed: (1) the preparation and iodocyclization of the unsaturated carbonimidothioate 2, and (2) the preparation, rearrangement, and subsequent iodocyclization of unsaturated carbonimidate 8. The alkene functionalization reactions allow a high measure of regio- and stereochemical control over the placement of the eventual amino and hydroxy groups.

Original languageEnglish (US)
Pages (from-to)5072-5076
Number of pages5
JournalJournal of Organic Chemistry
Issue number26
StatePublished - Dec 1984

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


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