期刊
TETRAHEDRON LETTERS
卷 58, 期 18, 页码 1738-1741出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.03.053
关键词
3-Hydroxy-2-hexanone; 2,3-Hexanediol; Aggregation pheromone; Cerambycid; Hypervalent iodine
资金
- Programa de Desarrollo de Ciencias Basicas (PEDECIBA) [PNUD/URU/06/004]
- Agenda Nacional de Investigacion e Innovacion (ANII)
- Comision Sectorial de Investigacion Cientifica (CSIC - UdelaR)
The synthesis of 3-hydroxy-2-hexanone and 2,3-hexanediol, two components of the aggregation pheromone of several cerambycid species, is disclosed in here. Starting from 2-hexanone, through an alpha-hydroxylation using (diacetoxyiodo)benzene, 3-hydroxy-2-hexanone is obtained in good yield. Further reduction of this compound, gives 2,3-hexanediol in excellent yield. A study of the alpha-hydroxylation reaction of several alkylketones using an hypervalent iodine reagent is also disclosed in here. The synthesis of optically active compounds (R)- and (S)-3-hydroxy-2-hexanone was achieved starting from 2-hexanone with nitrosobenzene and and D-proline respectively, in several reaction media. (C) 2017 Elsevier Ltd. All rights reserved.
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