1643775-38-5Relevant academic research and scientific papers
Iridium-Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic α-Alkoxy Ketones
Jiang, Xingyu,Chen, Wenyong,Hartwig, John F.
, p. 5819 - 5823 (2016)
The asymmetric alkylation of acyclic ketones is a longstanding challenge in organic synthesis. Reported herein are diastereoselective and enantioselective allylic substitutions with acyclic α-alkoxy ketones catalyzed by a metallacyclic iridium complex to form products with contiguous stereogenic centers derived from the nucleophile and electrophile. These reactions occur between allyl methyl carbonates and unstabilized copper(I) enolates generated in situ from acyclic α-alkoxy ketones. The resulting products can be readily converted into enantioenriched tertiary alcohols and tetrahydrofuran derivatives without erosion of enantiomeric purity.
One-pot asymmetric synthesis of substituted tetrahydrofurans via a multicatalytic benzoin/Michael/acetalization cascade
He, Gu,Wu, Fengbo,Huang, Wei,Zhou, Rui,Ouyang, Liang,Han, Bo
supporting information, p. 2311 - 2319 (2014/07/21)
A sequential benzoin/Michael/acetalization tandem reaction catalyzed by NHC and amine together has been developed to assemble aromatic aldehydes and enals into chiral tetrahydrofuran derivatives bearing multiple functional groups and stereogenic centers with high stereoselectivity of up to 95:5 dr and 96% ee. The high yield and stereocontrol of this process may be due to both acid-promoted symmetrization of racemic acyloins and iminium ion activation of enals.
