γ-Substituted siloxypyrrole derivatives 5-7 have been synthesized by direct alkylation of N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole 1. These underwent subsequent alkylation with alkyl halides or aldehydes to produce γ,γ-disubstituted α,β-unsaturated lactam intermediates in good yields. Oxidative cleavage of the C(3)-C(4) bond within the lactam moiety gave rise to a number of α-substituted α-amino acids. These include racemic α-methylphenylalanine 14, α-benzylphenylalanine 15, α-benzylserine 18 and α- methylthreonine 21.

γ-Substituted pyrrole-based silyl dienol ethers as aα-amino acid enolate equivalents: A versatile entry to racemic α-substituted α-amino acids / Zanardi, F.; Battistini, L.; Rassu, G.; Cornia, M.; Casiraghi, G.. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 19(1995), pp. 2471-2475.

γ-Substituted pyrrole-based silyl dienol ethers as aα-amino acid enolate equivalents: A versatile entry to racemic α-substituted α-amino acids

Zanardi F.;Battistini L.;Cornia M.;Casiraghi G.
1995

Abstract

γ-Substituted siloxypyrrole derivatives 5-7 have been synthesized by direct alkylation of N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole 1. These underwent subsequent alkylation with alkyl halides or aldehydes to produce γ,γ-disubstituted α,β-unsaturated lactam intermediates in good yields. Oxidative cleavage of the C(3)-C(4) bond within the lactam moiety gave rise to a number of α-substituted α-amino acids. These include racemic α-methylphenylalanine 14, α-benzylphenylalanine 15, α-benzylserine 18 and α- methylthreonine 21.
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: http://hdl.handle.net/11381/2885002
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 21
  • ???jsp.display-item.citation.isi??? 21
social impact