ChemInform Abstract: Stereocontrolled Reactions Through Heterocyclic Intermediates

Abstract

- New methods of double bonds halofunctionalization of allylic and homoallylic alcohol and amine derivatives have been developed. Carbonates, imidates, urethanes and amides have been cyclized to heterocyclic intermediates whose hydrolysis leads to diols, triols and aminoalcohols. This method has been applied to the synthesis of deoxyaminosugars (ristosamine and daunosamine), sphinganines, sphingosine and 2-amino-2-deoxytetritols. Moreover the use of chiral auxiliaries allows to obtain easily separable diastereomeric mixtures of heterocyclic intermediates, useful for the synthesis of biologically active compounds such as propranolol and GABOB.