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 (Research - C1) |
| ISSN: | 1873-3581 |
| Keywords: | photodecarboxylation; phthalimides; photochemistry; amino acids; photoinduced electron transfer |
| 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% |
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