期刊
TETRAHEDRON
卷 67, 期 2, 页码 408-416出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.11.025
关键词
Halocompounds; ATRC; gamma-Lactams; CuCl; Ascorbic acid
资金
- Ministero dell'Istruzione, dell'Universita e della Ricerca (MIUR) [200708J9L2A-005, 20085E2LXC-004, 20085E2LXC-003]
A 'green' ARGET-ATRC, for the CuCl[PMDETA] catalysed cyclo-isomerization of N-allyl-alpha-polychloroamides to gamma-lactams is described. The process works efficiently (yields 78-96%), uses a bio-solvent, as ethanol, and exploits the reducing feature of ascorbic acid to limit, at a low level (2-4%), the amount of catalyst. To preserve the efficacy of the catalytic cycle, addition of Na2CO3 is essential, which quenches the HCl released during the CuCl[PMDETA] regeneration step. Profitable features of the process are: mild reaction temperatures (25-37 degrees C), relatively short reaction times (usually 5 h) and low solvent volumes (2 mmol of substrate/mL of ethanol). The method, upon stoichiometric adjustment, was also used for the synthesis of alpha,beta-unsaturated-gamma-lactams from N-(2-chloroallyl)-alpha-polychloroamides, via a tandem process involving an ATRC and a reductive [1,2]-elimination. (C) 2010 Elsevier Ltd. All rights reserved.
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