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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 shu

Asymmetric Synthesis of L-menthol

1.
a Analytical and Testing Center, Ji'nan University, Guangzhou 510632, China;
2.
b Guangdong Food Industry Institute, Guangzhou 510308, China;
3.
c School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China

Corresponding author: WANG Lin,
Received Date: 25 September 2014
Available Online: 13 January 2015
Fund Project: 广东省教育部产学研结合项目(2011A090200039) (2011A090200039)广东省自然科学基金重点项目(S2013020013091)资助 (S2013020013091)

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.
- L-menthol,
- asymmetric hydrogenation,
- enantioselectivity,
- chiral ligand
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