90122-46-6Relevant articles and documents
Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols
Musolino, Stefania F.,Ojo, O. Stephen,Westwood, Nicholas J.,Taylor, James E.,Smith, Andrew D.
supporting information, p. 18916 - 18922 (2016/12/26)
The non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.
STEREOCONTROLLED CONSTRUCTION OF A SPIRO FUSED BICYCLOOCTANE RING SYSTEM BY THE INTRAMOLECULAR DOUBLE MICHAEL REACTION
Ihara, Masataka,Toyota, Masahiro,Fukumoto, Keiichiro,Kametani, Tetsuji
, p. 2167 - 2170 (2007/10/02)
The lithium enolate from the cyclohexenone (8) possessing the α,β-unsaturated ester moiety caused an intramolecular double Michael reaction to produce stereoselectively the spiro fused bicyclo-octane (10).