Aug 2026· Organic Letters· Vol 28 36, pp.
11379-11385
· 0 citations· 67 references
Medicine
Abstract
Reported herein is a stereoselective synthesis of 9-aryl-1-vinyl-tetrahydro-β-carbolines via a Pictet-Spengler reaction. This reaction proceeds via Brønsted acid-catalyzed cyclization of N-indole-tethered allenamides with >20:1 dr under mild conditions, while chiral phosphoric acid catalysis installs the C-N axial chirality with high enantioselectivity (up to 98% ee). An ortho-amide directing group and proper choice of catalyst prove crucial for the stereocontrol. Furthermore, divergent derivatizations of the products, particularly elaboration of the vinyl group, highlight the synthetic utility of this protocol.
A regio-, diastereo-, and enantioselective Pd-catalyzed allylation of the lithium salts of 6-membered cyclic allylboronates is reported. The system relies on the use of a commercially available C 2-symmetric chiral bisphosphine ligand and gives access to borylated 1,5-dienes featuring vicinal 3,4-cis tertiary stereocen...
R. Popov, Cheng Zhang, Laure Guénée et al.· JACS Au· 0 citations
Here we report the asymmetric Friedel-Crafts reaction between compounds α-aryl-α-fluoro-1,3-indanediones and indoles, catalyzed by an efficient chiral phosphoric acid catalyst. Using this methodology, a series of cyclic β-fluoroalcohols bearing two adjacent chiral centers were synthesized in up to 95% yield, with excel...
Xing-Pin Wei, Dan Li, Fen Gao et al.· Journal of Organic Chemistry· 0 citations
A palladium-catalyzed asymmetric synthesis of 3-substituted tetrahydroquinolines (THQs) through a C–C cleavage/C–C coupling sequence has been developed. By employing Pd(OAc)2/Josiphos L7 as the catalyst, an array of chiral tetrahydroquinolines bearing a C3-ketone pendant was afforded in good to excellent yields and e...
Cheng-Yu Li, Xiao-Jing Liu, Zhen-Ting Mao et al.· Organic Letters· 0 citations
Chiral arylvinyl-substituted 3-hydroxy-5-oxo esters are valuable motifs in pharmaceuticals, yet their enantiocontrolled synthesis remains challenging. Herein, we report a biocatalytic system using ketoreductases (KREDs) for the highly C3-selective reduction of arylvinyl-substituted 3,5-dicarbonyl esters. Through semira...
Xiao-Qiu Wu, Ming-Yu Zhang, Ming-Yang Yao et al.· Organic Letters· 0 citations
7-membered spirobenzazepinoindole frameworks constitute an important family of heterocyclic skeletons with broad utility in pharmaceutical research. Despite their value, the stereoselective synthetic routes toward chiral gem-difluorinated spirobenzazepinoindoles remain unexplored, and a general, efficient constructio...
Hui-Qiao Song, Yan-Ping Gao, Yi Hu et al.· Organic Letters· 0 citations
This study reports an optimized method for the synthesis of spiro-1,2-dihydropyridines via the cycloisomerization of 3-aza-1,5-enynes, catalyzed by heterogeneous gold(I)–polyoxometalate (POM) hybrids. By replacing traditional homogeneous catalysts with these hybrid systems, we achieved high yields (up to 82% isolated)...
Titien Simon, Fabian Schlimpen, P. de Frémont et al.· Beilstein Journal of Organic...· 0 citations
We use cookies to run the site and, with your consent, for analytics and to show ads.
See our Cookie Policy.
