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 conditions
2001
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]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/58445
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 12
  • ???jsp.display-item.citation.isi??? 8
social impact