1376710-72-3Relevant articles and documents
Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones
Lee, Jeonghyo,Wang, Sibin,Callahan, Miranda,Nagorny, Pavel
supporting information, p. 2067 - 2070 (2018/04/16)
This work describes the development of a new single-pot copper(II)-catalyzed decarboxylative Michael reaction between β-keto acids and enones, followed by in situ aldolization, which results in highly functionalized chiral and achiral cyclohexenones. The achiral version of this Robinson annulation features a hitherto unprecedented Michael reaction of β-keto acids with sterically hindered β,β′-substituted enones and provides access to all carbon quaternary stereocenter-containing cyclohexenones (11 examples, 43-83% yield). In addition, an asymmetric chiral bis(oxazoline) copper(II)-catalyzed single-pot Robinson annulation has been devised for preparing chiral cyclohexenones, including some products that contain vicinal stereocenters (5 examples, 65-85% yield, 84-94% ee). This latter protocol has been successfully applied to the enantioselective formation of the oxygenated 10-nor-steroid core from readily available starting materials.
Highly efficient synthesis of chiral aromatic ketones: Via Rh-catalyzed asymmetric hydrogenation of β,β-disubstituted enones
Zhang, Tao,Jiang, Jun,Yao, Lin,Geng, Huiling,Zhang, Xumu
supporting information, p. 9258 - 9261 (2017/08/22)
A succinct and efficient protocol was developed for the synthesis of chiral aromatic ketones via asymmetric hydrogenation of β,β-disubstituted enones with rhodium catalysts based on chiral bisphosphine thiourea ligands. A series of substrates (17 examples) was smoothly catalyzed to afford the corresponding chiral aromatic ketones in high conversions (>99%) with excellent enantioselectivities (up to 96% ee).
Highly enantioselective asymmetric hydrogenation of (E)-β,β- disubstituted α,β-unsaturated Weinreb amides catalyzed by Ir(i) complexes of SpinPhox ligands
Shang, Jian,Han, Zhaobin,Li, Yang,Wang, Zheng,Ding, Kuiling
, p. 5172 - 5174 (2012/06/18)
The Ir(i) complexes of chiral spiro phosphino-oxazoline ligands (SpinPhox) have demonstrated good to excellent enantioselectivity in the asymmetric hydrogenation (AH) of a variety of (E)-β,β-disubstituted α,β-unsaturated N-methoxy-N-methylamides, affording the corresponding optically active Weinreb amides with up to 97% ee.
