171898-22-9Relevant academic research and scientific papers
Furan-, pyrrole-, and thiophene-based siloxydienes for syntheses of densely functionalized homochiral compounds
Casiraghi,Rassu
, p. 607 - 626 (1995)
This review describes the methods of preparation and use of 2-(trimethylsiloxy)furan, N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole, and certain substituted analogues and congeners, including novel 2-(tert-butyldimethylsiloxy)thiophene, to synthesize complex carbohydrates, azasugars, polyhydroxylated alkaloids, C-glycosylated α-amino acids, amino acids bearing quaternary chiral carbon atoms, and thiosugars. Especially emphasized is the preparation of enantiomerically pure compounds of biological interest. Some mechanistic insights are presented.
γ-Substituted pyrrole-based silyl dienol ethers as α-amino acid enolate equivalents: a versatile entry to racemic α-substituted α-amino acids
Zanardi, Franca,Battistini, Lucia,Rassu, Gloria,Cornia, Mara,Casiraghi, Giovanni
, p. 2471 - 2476 (2007/10/02)
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.
