| 186 | 0 | 8 |
| Downloads | Citas | Reads |
Asymmetric catalysis has become a highly impactful strategy in organic synthesis,providing efficient and versatile tools for the construction of complex chiral molecules. According to catalyst origin and characteristics,asymmetric catalysis can be categorized into three major categories: Enzymatic catalysis,transition-metal catalysis,and small-molecule organocatalysis.Among them,organocatalysts based on small organic molecules have attracted substantial attention due to their low molecular weight,high structural tunability,excellent stability,and environmentally friendly nature. They were particularly powerful for enabling the efficient formation of challenging chiral C—C bonds under mild conditions,thereby playing a key role in sustainable synthesis.The asymmetric Aldol reaction,a classical transformation for the synthesis of β-hydroxy carbonyl compounds,has become a powerful platform for the preparation of natural products,pharmaceuticals,and functional materials. In this review,we summarized recent advances(primarily from 2022 to the present) in small-molecule organocatalytic asymmetric Aldol reactions,organized by catalyst structural classes.Emphasis was placed on amino acids and their derivatives,thiourea-based hydrogen-bonding organocatalysts,and other small organic catalysts including macrocycles,porous organic cages,covalent organic frameworks,and nanostructured systems.Representative studies were discussed with respect to catalyst design concepts,reaction efficiency and stereocontrol(yields,enantioselectivity,and diastereoselectivity),green reaction media,and catalyst recyclability. Challenges and future perspectives were also highlighted,aiming to offer insights and guidance for continued progress in organocatalytic asymmetric Aldol chemistry.
[1]Koskinen A M P,Karisalmi K. Chem. Soc. Rev.,2005,34(8):677.
[2]Pousse G,Cavelier F,Humphreys L,Rouden J,Blanchet J.Org.Lett.,2010,12(16):3582-3585.
[3]Hajos Z G,Parrish D R. J. Org. Chem.,1974,39(12):1615-1621.
[4]Eder U,Sauer G,Wiechert R.Angew.Chem.Int.Ed.,1971,10(7):496-497.
[5]Al-momani L,Lataifeh A. Ind. Eng. Chem. Res.,2022,61(6):2417-2424.
[6]Lakhani P,Modi C K.Mol.Catal.,2022,525:112359.
[7]Yilmaz D G,Aydogan F,Yolacan C.J.Heterocycl.Chem.,2022,59(7):1169-1179.
[8]Uyanik A,Sahin O,Akceylan E,Eymur S,Uyanik I,Yilmaz M.Russ.J.Gen.Chem.,2022,92(11):2390-2399.
[9]Naeimi S S,Salehi P,Bararjanian M. J. Iran. Chem. Soc.,2022,19(8):3407-3416.
[10]Zalewska K,Zakrzewska M E,Branco L C. Catalysts,2022,12(1):47.
[11]Xu N,Su K Z,El-sayed E M,Ju Z F,Yuan D Q.Chem.Sci.,2022,13(12):3582-3588.
[12]Lv X X,Liu N,Chen F,Zhang H,Du Z H,Wang P,Yuan M,Da C S. Org. Biomol. Chem.,2023,21(43):8695-8701.
[13]Begum Z,Seki C,Okuyama Y,Kwon E,Uwai K,Tokiwa M,Tokiwa S,Takeshita M,Nakano H. RSC Adv.,2023,13(2):888-894.
[14]Hikawa R,Shimogaki M,Kano T.Chem.Commun.,2023,59(54):8424-8427.
[15]Mastai Y,Abuaf M,Das S. RSC Adv.,2023,13(3):1580-1586.
[16]Singh S,Deep A.Chem.Select,2023,8(1):e202202379.
[17]FaragóT,Remete A M,Szatmári I,Ambrus R,PalkóM.RSC Adv.,2023,13(28):19356-19365.
[18]Easwar S,Reddy S R,Kumari K,Bhati M,Madhukar R S,Khan A G H,Janjani P.New J.Chem.,2023,47(36):17042-17050.
[19]Peme T,Brady D,Shumbula N P,Machumele K,Moloto N,Adams T,Makatini M M. Catalysts,2024,14(11):826.
[20]Yıldız T,Hasdemir B,Ya sa H,Ba spınar K H.ACS Omega,2024,9(8):8913-8921.
[21]Raglione V,Palmeri F,Vetica F,D'annibale A. Tetrahedron Green Chem.,2025,6:100086.
[22]Bonjoch J,Bradshaw B.Synlett,2012,3:337-356.
[23]Bui T,Barbas C F. Tetrahedron Lett.,2000,41(36):6951-6954.
[24]Inomata K,Akahane Y.Heterocycles,2022,105(1):566.
[25]Li C L,Zhan M R,Wang Z X,Gao H,Yang Y,Gou H Q.Catal.Lett.,2024,154(4):1420-1430.
[26]Li C L,Lai C Y,Zhan M R,Zhao X N,Dong W Y,Liu J Q,Wang P B.Russ.J.Org.Chem.,2025,61(2):338-345.
[27]Chao Y H,Jamwal P,Ananda R G,Gurubrahamam R,Chen K.Org.Lett.,2024,26(23):4938-4944.
[28]Cao S X,Li J T,Yan T S,Han J,He Z J. Org. Chem.Front.,2022,9(3):643-648.
[29]Gupta E,Vaishanv N K,Kumar S,Purshottam R K,Kant R,Mohanan K. Beilstein J. Org. Chem.,2022,18:217-224.
[30]Chen F E,Xiao Y C,Chen X P,Liu J X,Li H Y.Adv.Synth.Catal.,2022,364:2067-2071.
[31]Meso G,Gregorich D,Waite A J,Smith S,Liu L N,Cortez J,Harris E,Baluyut R D,Correa N,Liang J,Liu Y.Chem Cat Chem,2023,15(11):e202300012.
[32]Ozgun U,Sirit A,Genc H N.J.Inclusion Phenom.Macrocycl.Chem.,2024,104(11/12):623-632.
[33]Zhang K,Tang X H,Yang X,Wu J L,Guo B Y,Xiao R,Xie Y,Zheng S R,Jiang H W,Fan J,Zhang W G,Liu Y,Cai S L. ACS Appl. Mater. Interfaces,2024,16(8):10661-10670.
Basic Information:
DOI:10.13822/j.cnki.hxsj.2025.0235
China Classification Code:O621.251
Citation Information:
[1]WANG Yu,LUO Qian-ting,HE Hua-feng ,et al.Recent Advances in Organocatalytic Asymmetric Aldol Reactions[J].Chemical Reagents,2026,48(02):18-29.DOI:10.13822/j.cnki.hxsj.2025.0235.
Fund Information:
国家自然科学基金项目(22201100); 山东省自然科学基金项目(ZR2022QB183); 山东省高等学校青创科技支持计划项目(2024KJG031)