Journal
TETRAHEDRON LETTERS
Volume 58, Issue 33, Pages 3234-3237Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.07.007
Keywords
Umpolung; Metallation reaction; Electrophiles; Silyl enol ether
Categories
Funding
- Consejo Nacional de Ciencia y Tecnologia [CONACyT 360339]
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A new protocol to obtain 3-substituted 2-cyclohexenones, was developed by reversing the chemical reactivity of 2-cyclohexenone. One-pot synthesis of 3-substituted 2-cyclohexenones can be achieved by treatment of 3-phenylthiosilyl enol ether with a mixture of t-BuLi/HMPA that allows hydrogen-selective exchange in presence of reactive electrophiles such as aldehydes, ketones and alkyl halides. This affords the corresponding product in moderate overall yield, after silyl enol ether cleavage and concomitant thiophenol elimination initiated with TBAF. (C) 2017 Elsevier Ltd. All rights reserved.
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