摘要
本文利用本课题组设计合成的SunPhos配体对几类多羰基官能化酮的不对称氢化进行了研究，实现了化学选择性和立体选择性的同时控制。主要工作内容包括:
1.通过比较一系列β-酮酸衍生物氢化反应速率，发现在EtOH中β-酮酰胺的氢化反应速率略快于β-酮酸酯，而在THF中大多数β-酮酰胺氢化反应速率远远快于β-酮酸酯。在此基础上，我们实现了3-氧代戊二酸衍生物的不对称氢化，对映选择性高达98.1%。同时，首次实现了同一分子内含有双β-酮酸衍生物体系的化学选择性和对映选择性氢化。通过研究这类底物氢化反应中的溶剂效应和底物活泼亚甲基上的取代基效应，我们发现在CH_2Cl_2、丙酮、二氧六环等非质子溶剂中，很多底物(特别是未取代的底物)也能够顺利氢化。而且，对某些底物还出现了产物构型在不同溶剂中翻转的现象。我们提出了烯醇式氢化的反应途径来解释这些现象。
2.利用乙酰丙酮和β-酮酰胺在THF中氢化反应活性的巨大差别，实现了3,5-二氧代己酰胺的C3-羰基选择性氢化。通过筛选不同的3,5-二氧代己酸衍生物，发现二乙基酰胺在THF中能够顺利实现3-羰基的高选择性不对称氢化，而且ee值最高。在此基础上，进而实现了一系列取代的3,5-二氧代二乙基酰胺的不对称氢化，化学选择性接近100%，对映选择性达97.4%。同时还意外地发现，6-杂原子的引入会导致5-羰基被部分或全部被氢化。在一些酸性添加剂(BF_3·Et_2O, HBF_4,H_2SO_4, TsOH·H_2O等)或混合溶剂的作用下，可以促进3,5-二羰基的一步全部氢化，而且可以通过使用不同构型的配体、添加不同性质的溶剂来调节3,5-二羰基氢化产物的syn-, anti-立体化学控制，其中syn-产物的ee值均在99%以上，syn:anti可达90:10。
3.基于杂原子(Cl, O)对3,5-二氧代羧酸衍生物氢化中C3-化学选择性有反常的影响，我们对羰基邻近含有O, S, N, Cl, F等杂原子的1,3-二酮的选择性不对称氢化进行了研究后发现，杂原子的存在可以“活化”邻近的羰基，同时分子内氢键对这一活化作用进行了解释。我们在THF中实现了一系列邻近带有苄氧基，苯砜基和邻苯二甲酰亚胺基的β-二酮的高选择性氢化，化学选择性可达95%，ee值均在95~99%之间。此外，还研究了2,4-二氧代羧酸酯和酰胺的不对称氢化，化学选择性均在90%以上，对映选择性中等(78-89%)。
通过本论文的研究，我们认识到在多官能化羰基酮的氢化反应中，具有一定配位性的配体或者溶剂能够起到调节不同基团竞争性配位能力的作用。同时，在多个羰基存在的情况下，能够借助配位溶剂或者底物自身一些杂原子官能团来改变目标羰基周围的配位环境，从而实现多羰基化合物的高立体和化学选择性氢化。
In this dissertation, we actualized the highly chemo-and enantioselectivehydrogenation of some poly-functionalized ketones with Ru-SunPhos complexes. Themain contents fall into three sections:
1. Upon comparing the hydrogenation rates of various β-ketocarboxylic acidderivatives, β-ketoamides were found to be hydrogenated slightly faster thanβ-ketoesters in EtOH. In THF, the rate differences were enormously increased thatβ-ketoamides were hydrogenated smoothly while β-ketoesters almost intact. Based onthese findings, a series of3-oxoglutaric acid derived with ester and amide moieties onthe two ends were hydrogenated to3-hydroxyl products with high enantioselectivities(up to98.1%ee). Unconventional solvent and substituent effects were also discoveredwhen these substrates were hydrogenated smoothly in uncommon solvents such asTHF, CH_2Cl_2, acetone and dioxane with high enantioselectivities. Possible catalyticcycle through an enol intermediate was proposed to explain the different reactivity ofthese1,3,5-tricarbonyl substrates in the tested solvents. More pronounced solventeffects were discovered concerning the substituted substrates: ee’s increased from ca.20%in EtOH or THF to90%in acetone; inversion of products’ configurations wereobserved when the solvent was changed from EtOH to THF or acetone; and mixedsolvent systems can give better enantioselectivities than a single solvent.
2. By screening the derivative moieties of3,5-diketo hexanoic acid, diethylamides were found to be hydrogenated smoothly at the C3-carbonyl with highenantioselectivities in THF, based on which we achieved a general hydrogenationmethod for the C3-selective reduction of3,5-diketo amides (26examples, up to97.4%ee and100%chemoselectivity). The heteroatoms on the6-positions lead to partial orcomplete hydrogenation of the C5-carbonyls. Moreover, we also found that acidicadditives like BF_3·Et_2O, HBF4, H_2SO_4and TsOH·H_2O promoted the3,5-doublehydrogenation in favour of the syn-isomers. By employing ligands with opposite configurations or different types of solvents, the syn and anti selectivity werecontrolled efficiently. In the best cases, the syn:anti ratio was up to90:10and the eevalues of syn isomers were>99%.
3. Upon reinvestigation into the unusual effect of C6-heteroatom on thechemoselectivity in the hydrogenation of3,5-diketoamides, we found the “activation”of the central carbonyls in1,3-diketones. The heteroatoms (O, S, N, halogens)substituted1,3-diketones were hydrogenated selectively at the carbonyls adjacent tothe heteroatoms in THF with high level of chemo-and enantioselectivity.2,4-Diketoacid esters and amides were also hydrogenated selectively at C2-carbonyls with goodchemoselectivity and moderate enantioselectivity.
In summary, the coordinating ligands or solvents played some roles inmodulating the coordination environment of the target carbonyls in the asymmetrichydrogenation of polycarbonyl substrates. Therefore, it is possible to enhance thechemo-and enantioselectivity in hydrogenation of polycarbonyl compounds.
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