NDLI: A formal [3,3]-sigmatropic rearrangement route to quaternary alpha-vinyl amino acids: use of allylic N-PMP trifluoroacetimidates.

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A formal [3,3]-sigmatropic rearrangement route to quaternary alpha-vinyl amino acids: use of allylic N-PMP trifluoroacetimidates.

Content Provider	Semantic Scholar
Author	Berkowitz, David B. Wu, Bin Rong Li, Huijie
Copyright Year	2006
Abstract	Pd(II)-mediated rearrangement of allylic N-PMP (p-methoxyphenyl) trifluoroacetimidates provides the first formal sigmatropic route to quaternary, alpha-vinylic amino acids, potential suicide substrates for PLP enzymes. The amino acid side chains enter via transition-metal-mediated C-C bond constructions, including (i) Cu(I)-mediated conjugate addition (Ala); (ii) Pd(0)/AsPh3-mediated Stille coupling (allyl-Gly, Phe, DOPA, m-Tyr); and (iii) Pd(0)/Pt-Bu3-mediated Negishi coupling (Leu). In the synthesis of the DOPA decarboxylase inactivator, alpha-vinyl-m-tyrosine, the new N-PMP trifluoroacetimidate rearranges much more efficiently than the corresponding trichloroacetimidate.
Starting Page	1479
Ending Page	1479
Page Count	1
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=1014&context=chemistryberkowitz
PubMed reference number	16494487v1
Volume Number	8
Issue Number	5
Journal	Organic letters
Language	English
Access Restriction	Open
Subject Keyword	Alanine Amino Acid Metabolism, Inborn Errors Amino Acids Carboxy-Lyases DNA Sequence Rearrangement DOPA decarboxylase Immunostimulating conjugate (antigen) Leucine PTHLH protein, human Phenylalanine Polyvinyl Chloride Tyrosine allylic sulfur ylide alpha-Mannosidosis cytidine S-3,4-dioctadecoxybutylphosphinato(methylene phosphonate) peroxisome membrane targeting sequence binding promegapoietin trichloroacetamide type I interferon receptor
Content Type	Text
Resource Type	Article

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