Reductive lithiation of a distereoisomeric mixture of bicyclic oxazolidines followed by reaction with alkyl halides afforded aminoalcohols in a highly syn-selective fashion. Reductive lithiation occurs with racemization at the benzylic carbon atom; the observed diastereoselectivities are rationalized in terms of a pair of rapidly equilibrating diastereoisomeric organolithium intermediates, one of which reacts preferentially under appropriate reaction conditions
Diastereoselective Alkylation of a-Amino-Substituted Benzyllithiums, Tetrahedron Letters / Azzena, Ugo Gavino; Luciano, Pilo; Elisabetta, Piras. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 42:(2001), pp. 129-131. [10.1016/S0040-4039(00)01898-0]
Diastereoselective Alkylation of a-Amino-Substituted Benzyllithiums, Tetrahedron Letters
AZZENA, Ugo Gavino;
2001-01-01
Abstract
Reductive lithiation of a distereoisomeric mixture of bicyclic oxazolidines followed by reaction with alkyl halides afforded aminoalcohols in a highly syn-selective fashion. Reductive lithiation occurs with racemization at the benzylic carbon atom; the observed diastereoselectivities are rationalized in terms of a pair of rapidly equilibrating diastereoisomeric organolithium intermediates, one of which reacts preferentially under appropriate reaction conditionsI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
