Highly efficient asymmetric synthesis of 3-indolyl(hydroxy)acetates via Friedel-Crafts alkylation of indoles. 2009

Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.

An efficient enantioselective Friedel-Crafts alkylation of indoles to ethyl glyoxylate catalyzed by chiral N,N'-dioxide-Sc(III) complex was developed. The corresponding 3-indolyl(hydroxy)acetates compounds were afforded in good yields with high enantioselectivities (up to 95% ee).

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D008024 Ligands A molecule that binds to another molecule, used especially to refer to a small molecule that binds specifically to a larger molecule, e.g., an antigen binding to an antibody, a hormone or neurotransmitter binding to a receptor, or a substrate or allosteric effector binding to an enzyme. Ligands are also molecules that donate or accept a pair of electrons to form a coordinate covalent bond with the central metal atom of a coordination complex. (From Dorland, 27th ed) Ligand
D008670 Metals Electropositive chemical elements characterized by ductility, malleability, luster, and conductance of heat and electricity. They can replace the hydrogen of an acid and form bases with hydroxyl radicals. (Grant & Hackh's Chemical Dictionary, 5th ed) Metal
D008956 Models, Chemical Theoretical representations that simulate the behavior or activity of chemical processes or phenomena; includes the use of mathematical equations, computers, and other electronic equipment. Chemical Models,Chemical Model,Model, Chemical
D010087 Oxides Binary compounds of oxygen containing the anion O(2-). The anion combines with metals to form alkaline oxides and non-metals to form acidic oxides. Oxide
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D002626 Chemistry, Pharmaceutical Chemistry dealing with the composition and preparation of agents having PHARMACOLOGIC ACTIONS or diagnostic use. Medicinal Chemistry,Chemistry, Pharmaceutic,Pharmaceutic Chemistry,Pharmaceutical Chemistry,Chemistry, Medicinal
D006038 Glyoxylates Derivatives of glyoxylic acid (the structural formula C2H2O3), including its salts and esters.
D000085 Acetates Derivatives of ACETIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the carboxymethane structure. Acetate,Acetic Acid Esters,Acetic Acids,Acids, Acetic,Esters, Acetic Acid
D000478 Alkylation The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group. Alkylations

Related Publications

Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
September 2010, Organic & biomolecular chemistry,
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
August 2011, The Journal of organic chemistry,
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
December 2021, Chemical communications (Cambridge, England),
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
October 2016, The Journal of organic chemistry,
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
May 2017, Angewandte Chemie (International ed. in English),
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
May 2019, Tetrahedron letters,
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
March 2022, Organic & biomolecular chemistry,
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
October 2015, Organic letters,
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
August 2009, Chirality,
Yonghai Hui, and Qi Zhang, and Jun Jiang, and Lili Lin, and Xiaohua Liu, and Xiaoming Feng
August 2020, The Journal of organic chemistry,
Copied contents to your clipboard!