Abstract: The present invention relates to 2-substituted-1-hydroxyindoles of the following formula: ##STR1## wherein, R.sup.1 is an electron withdrawing group,R.sup.2 is an alkenyl having 2-10 carbon atoms, and N-substituted .alpha.-iminobenzyl group wherein the substituents are selected from the group consisting of phenyl, anilino and dimethylamino, an unsubstituted aromatic group, and an aromatic group having meta or para substituents which are nitro, trifluoromethyl, fluoro, formyl, hydroxyiminomethyl and carbamoyl,R.sup.3 is a halogen atom, andn is 0, 1, or 2,provided that when R.sup.2 is either phenyl or nitro substituted phenyl and n is 0, then R.sup.1 is not cyano.

Abstract: A method for the preparation of chiral 2-amino-1,3-diols is disclosed. The method involves four steps including performance of an aldol condensation with a chiral oxazolidinone on an aldehyde, treating the aldol condensation product with an alkali metal azide, treating the product with a borohydride reagent and reducing the azide to an amine.