左旋薄荷醇的不对称合成

应用化学, 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

王林 ^1, , 李焕勇 ^2, , 谭微 ^3, , 王三永 ^4, , 李春荣 ^5, , 杨定乔 ^6,

1.暨南大学分析测试中心广州510632

2.暨南大学分析测试中心广州510632

3.暨南大学分析测试中心广州510632

4.广东省食品工业研究所广州510308

5.广东省食品工业研究所广州510308

6.华南师范大学化学与环境学院广州510006

基金项目: 广东省教育部产学研结合项目(2011A090200039) the Natural Science Foundation of Guangdong Province(S2013020013091) the Industry-Academia Cooperation Project of the Ministry of Education of Guangdong Province(2011A090200039) 广东省自然科学基金重点项目(S2013020013091)

关键词：左旋薄荷醇 , 不对称氢化 , 对映选择性 , 手性配体

Asymmetric Synthesis of L-menthol

Keywords： L-menthol , asymmetric hydrogenation , enantioselectivity , chiral ligand

以4-羟基-2-丁酮和异丙叉丙酮为起始原料,经羟醛缩合、不对称氢化、羰基还原、钌催化氢化等4步反应制得左旋薄荷醇.总产率为33％,非对映体过量de值达到93％.详细探讨了铜催化剂及其用量、手性配体的选择、反应溶剂和时间等因素对胡薄荷烯酮不对称氢化反应的影响.中间体及目标化合物均通过了1HNMR、13C NMR和HRMS等技术手段的分析测定及结构表征.

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