Journal
TETRAHEDRON
Volume 73, Issue 39, Pages 5813-5819Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.08.035
Keywords
Ketoesters; Carbamoylsilanes; Amides; Addition; Synthetic methods
Categories
Funding
- Shanxi Province Foundation for Returness [0713]
- Natural Science Foundation of Shanxi Province [2012011046-9]
- Foundation of Shanxi Normal University, China [WL2016CXCY-YJ-30]
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The addition of N-methoxymethyl-N-organylcarbamoyl(trimethyl)silane to alpha-ketoesters in anhydrous toluene at 60 degrees C afforded alpha-alkoxycarbonyl-alpha-siloxy amides in high yields (75-96%). The methoxymethyl was used as an amino protecting group and could be easily converted into hydrogen atom by simple acid hydrolysis leading to alpha-alkoxycarbonyl-alpha-hydroxy secondary amides. (c) 2017 Elsevier Ltd. All rights reserved.
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