Journal
TETRAHEDRON LETTERS
Volume 57, Issue 30, Pages 3334-3338Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.06.064
Keywords
Mukaiyama oxidative cyclization; 2,5,5-Trisubstituted tetrahydrofuran; Metal catalysis
Categories
Funding
- FAPESP [13/02311-3]
- CNPq [477944/2013-2]
- CAPES
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [13/02311-3] Funding Source: FAPESP
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Aryl gem-disubstituted conjugated alkenols underwent oxidative cyclization affording 2,5,5-trisubstituted tetrahydrofurans in reasonable yields and good diastereoselectivities using the reductive termination variation of the Mukaiyama aerobic oxidative reaction. Under oxidative termination, the same alkenols produced diols and ketonic by-products via the double hydration and beta-scission competing pathways. Furthermore, the differences in alkenol reactivity under the reductive and oxidative termination conditions were investigated. (C) 2016 Elsevier Ltd. All rights reserved.
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