引用本文:
王林, 李焕勇, 谭微, 王三永, 李春荣, 杨定乔. 左旋薄荷醇的不对称合成[J]. 应用化学,
2015, 32(6): 641-646.
doi:
10.11944/j.issn.1000-0518.2015.06.140332
Citation: WANG Lin, LI Huanyong, TAN Wei, WANG Sanyong, LI Chunrong, YANG Dingqiao. Asymmetric Synthesis of L-menthol[J]. Chinese Journal of Applied Chemistry, 2015, 32(6): 641-646. doi: 10.11944/j.issn.1000-0518.2015.06.140332
Citation: WANG Lin, LI Huanyong, TAN Wei, WANG Sanyong, LI Chunrong, YANG Dingqiao. Asymmetric Synthesis of L-menthol[J]. Chinese Journal of Applied Chemistry, 2015, 32(6): 641-646. doi: 10.11944/j.issn.1000-0518.2015.06.140332
左旋薄荷醇的不对称合成
English
Asymmetric Synthesis of L-menthol
Abstract:
L-menthol was synthesized from the starting materials of 4-hydroxy-2-butanone and mesityl oxide in four steps consisting of aldol condensation,asymmetric hydrogenation,reduction of carbonyl group,and ruthenium catalyzed hydrogenation. The total yield is 33% and the diastereomeric excess is 93%.Furthermore,the effects of copper catalysts and their loading,chiral ligands,reaction time and solvents on the asymmetric hydrogenation of piperitenone were discussed in details. The intermediates and target compound were identified and characterized by 1H NMR,13C NMR and HRMS.
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Key words:
- L-menthol
- / asymmetric hydrogenation
- / enantioselectivity
- / chiral ligand
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