Photodecarboxylative additions of N-protected α-amino acids to N-methylphthalimide

Gallagher, Sonia, Hatoum, Fadi, Zientek, Nicolai, and Oelgemöller, Michael (2010) Photodecarboxylative additions of N-protected α-amino acids to N-methylphthalimide. Tetrahedron Letters, 51 (28). pp. 3639-3641.

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Abstract

Photoreactions involving N,N-dimethylated α-amino acid salts and N-methylphthalimide are dominated by photoreduction and acetone trapping. Only, N-phenyl glycinate underwent photodecarboxylative addition in a moderate yield of 30%. In contrast, N-acylated α-amino acid salts readily gave addition products in fair to high yields of 20–95%. Comparison experiments with N,N-dimethylacetamide and amino-/amido-containing phthalimides revealed the origin of the crucial electron-transfer step and the reactivity order NR3 » View the MathML source greater-or-equal, slanted RCONR2 was established.

Item ID: 16791
Item Type: Article (Refereed Research - C1)
Keywords: photodecarboxylation; phthalimides; photochemistry; amino acids; photoinduced electron transfer
ISSN: 1873-3581
Date Deposited: 05 May 2011 09:55
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030501 Free Radical Chemistry @ 20%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 50%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 30%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
Citation Count from Web of Science Web of Science 8
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