156713-08-5Relevant articles and documents
A Remarkable Inversion in Configuration of the Product Alcohols from the Asymmetric Reduction of ortho-Hydroxyacetophenones with B-Chlorodiisopinocampheylborane
Ramachandran, P. Veeraraghavan,Gong, Baoqing,Brown, Herbert C.
, p. 2141 - 2144 (1994)
Asymmetric reduction of o-hydroxyacetophenones with B-chlorodiisopinocampheylborane provides product alcohols with the opposite configuration compared to those produced in the reduction of the corresponding o-methoxyacetophenones.The implications of this result for organic synthesis are discussed.
An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode
Abazid, Ayham H.,Clamor, Nils,Nachtsheim, Boris J.
, p. 8042 - 8048 (2020/09/21)
The application of a triazole-substituted chiral iodoarene in a direct enantioselective hydroxylation of alkyl arenes is reported. This method allows the rapid synthesis of chiral benzyl alcohols in high yields and stereocontrol, despite its nontemplated nature. In a cascade activation consisting of an initial irradiation-induced radical C-H-bromination and a consecutive enantioconvergent hydroxylation, the iodoarene catalyst has a dual role. It initiates the radical bromination in its oxidized state through an in-situ-formed bromoiodane and in the second, Cu-catalyzed step, it acts as a chiral ligand. This work demonstrates the ability of a chiral aryl iodide catalyst acting both as an oxidant and as a chiral ligand in a highly enantioselective C-H-activating transformation. Furthermore, this concept presents an enantioconvergent hydroxylation with high selectivity using a synthetic catalyst.
New alkoxymethyl-functionalized pyridinium-based chiral ionic liquids: synthesis, characterization and properties
Gondal, Humaira Yasmeen,Mumtaz, Salma,Abbaskhan, Ahmed,Mumtaz, Nargis,Cano, Israel
, p. 2951 - 2963 (2020/03/23)
Abstract: An efficient solvent-free synthesis of a new family of functionalized chiral ionic liquids based on pyridinium cation has been developed from low-cost chiral terpenoid alcohols. An exhaustive characterization was performed using state-of-the-art
Water soluble Ru (II)–p-cymene complexes of chiral aroylthiourea ligands derived from unprotected D/L-alanine as proficient catalysts for asymmetric transfer hydrogenation of ketones
Sheeba, Mani Mary,Tamizh, Manoharan Muthu,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
, (2019/01/04)
The newfangled chiral aroylthiourea ligands (L1-L6) were produced from unprotected D/L-alanine and their water soluble Ru (II) organometallic catalysts (1–6) were designed from their reaction with [RuCl2(η6-p-cymene)]2. The analytical and spectral methods were used to confirm the structure of the ligands and complexes. The solid state structure of L1, 5 and 6 was confirmed by single crystal XRD. The organometallic compounds (1–6) catalyzed the asymmetric transfer hydrogenation of aromatic, heteroaromatic and bulky ketones to yield respective enantiopure secondary alcohols with admirable conversions (up to 99%) and attractive enantiomeric excesses (ee up to 98%), in presence of formic acid and triethylamine in water medium under non-inert atmospheric conditions.
