二酮的不对称催化还原反应研究进展

doi:10.6023/cjoc202207045

摘要/Abstract

手性二醇类化合物是一类重要的手性结构单元和手性中间体, 过渡金属催化的二酮类化合物的不对称氢化和氢转移反应是获得手性二醇最为直接高效的方法之一. 同时, 手性羟基酮作为二酮的不对称单还原产物, 也广泛应用于手性片段的构建, 其中环状二酮的去对称化甚至可一步构建多个手性中心. 从不同底物类型(1,2-/1,3-/1,4-)的二酮角度出发, 综述了近几十年来二酮类化合物的不对称氢化和氢转移反应研究进展, 着重讨论底物与催化剂配位模式对反应选择性的影响, 并对该领域未来的挑战和发展方向进行了展望.

关键词: 手性二醇, 手性羟基酮, 二酮类化合物, 不对称氢化, 不对称氢转移, 配位模式

Chiral diols are an integral part of chiral building blocks and synthetic intermediates. Transition metal-catalyzed asymmetric hydrogenation and transfer hydrogenation of diketones are recognized as one of the most straightforward and efficient methods for the preparation of enantiomerically enriched diols. Meanwhile, the mono-reduction product of diketones, chiral hydroxyketones, has wide application in chiral fragment construction as well, among which, desymmetrization of cyclic diketones possesses the capability of establishing multiple chiral centers in one step. In this paper, research progress of asymmetric hydrogenation and transfer hydrogenation of diketone compounds in recent decades is reviewed from the perspective of different substrate types (1,2-/1,3-/1,4-diketones), with emphasis on the influence of coordination mode between substrate and catalyst species on the stereoselectivity. In addition, future challenges and development tendencies in this field are summarized and prospected.

Key words: chiral diols, chiral hydroxyketone, diketones, asymmetric hydrogenation, asymmetric transfer hydrogenation, coordination mode

引用此文

张宇轩, 许立民, 卢岩, 张兆国. 二酮的不对称催化还原反应研究进展[J]. 有机化学, 2022, 42(10): 3221-3239.

Yuxuan Zhang, Limin Xu, Yan Lu, Zhaoguo Zhang. Progress in Asymmetric Catalytic Reduction of Diketones[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3221-3239.

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图/表 18

图式1. 1,2-二酮不对称氢转移反应中的动态动力学拆分过程

Scheme 1. Dynamic kinetic resolution process in the asymmetric transfer hydrogenation of 1,2-diketones

图式2. pH对反应效率和选择性的影响

Scheme 2. Effect of pH on reaction efficiency and selectivity

图式3. 碱存在条件下安息香的动态动力学拆分过程

Scheme 3. Dynamic kinetic resolution process of benzoin in the presence of a base

图式4. 反应过渡态中存在的非共价相互作用

Scheme 4. Noncovalent interactions in the transition state

图式5. (R,R)-1,2,4,5-二环氧戊烷的合成

Scheme 5. Synthesis of (R,R)-1,2,4,5-diepoxypentane

图式6. (R,R)-BDPBzP的合成

Scheme 6. Synthesis of (R,R)-BDPBzP

图式7. 埃博霉素D手性片段的合成

Scheme 7. Synthesis of Epothilone D chiral fragment

图式8. Ru-biphemp催化的乙酰丙酮的不对称氢化

Scheme 8. Ru-biphemp-catalyzed asymmetric hydrogenation of acetylacetone

图式9. Ru-biphemp催化的1,3-二酮不对称氢化及机理研究

Scheme 9. Ru-biphemp-catalyzed asymmetric hydrogenation of 1,3-diketones with mechanistic investigations

图式10. Ru-SunPhos催化的3,5-二氧代酰胺的不对称氢化

Scheme 10. Ru-SunPhos-catalyzed asymmetric hydrogenation of 3,5-dioxoamides

图式11. 杂原子形成的氢键对邻近羰基的“活化”作用

Scheme 11. Hydrogen bond “activation” of adjacent carbonyls by heteroatoms

图式12. BDPP(Skewphos)催化合成其相反构型的对映异构体

Scheme 12. BDPP(Skewphos)-catalyzed synthesis of its counter-configured enantiomer

图式13. 2-甲基-1,3-二酮的动态动力学拆分-不对称氢转移

Scheme 15. Dynamic kinetic resolution-asymmetric transfer hydrogenation of 2-methyl-1,3-diketones

图1. α,α-二取代1,3-二酮的不对称氢转移反应

Figure 1. Asymmetric transfer hydrogenation of α,α-disubstituted 1,3-diketones

图式14. 1-芳基-3-CF3-1,3-二酮的不对称氢转移反应

Scheme 14. Asymmetric hydrogen transfer reaction of 1-Aryl-3- CF3-1,3-diketones

图式15. 2,2,5-三取代-1,3-环己二酮的氢化去对称化环内酯化反应

Scheme 15. Hydrogenative desymmetrization and cyclic lactonization of 2,2,5-trisubstituted 1,3-cyclohexanediones

图式16. 2,2,5-三取代-1,3-环己二酮的氢化去对称化反应

Scheme 16. Hydrogenative desymmetrization of 2,2,5-trisubstituted 1,3-cyclohexanediones

图2. 炔基酮底物与催化剂芳环之间的C—H/π稳定化作用

Figure 2. Stabilizing C—H/π interaction between acetylenic ketone and aromatic ring of the catalyst

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