27312-31-8Relevant academic research and scientific papers
Dynamic Kinetic Asymmetric Transformation of Racemic Diastereomers: Diastereo- and Enantioconvergent Michael–Henry Reactions to Afford Spirooxindoles Bearing Furan-Fused Rings
Sohail, Muhammad,Tanaka, Fujie
, p. 21256 - 21260 (2021/08/23)
Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated the DYKAT in the diastereo- and enantio
Titanium(IV)-catalyzed stereoselective synthesis of spirooxindole-1-pyrrolines
Badillo, Joseph J.,Ribeiro, Carlos J. A.,Olmstead, Marilyn M.,Franz, Annaliese K.
supporting information, p. 6270 - 6273 (2015/02/19)
A stereoselective cyclization between alkylidene oxindoles and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (as low as 5 mol %) to afford spiro[3,3-oxindole-1-pyrrolines] in excellent yield (up to 99%) and diastereoselectivity (up to 99:1). Using a chiral scandium(III)-indapybox/BArF complex affords enantioenriched spirooxindole-1-pyrrolines where a ligand-induced reversal of diastereoselectivity is observed. This methodology is further demonstrated for the synthesis of pyrrolines from malonate alkylidene and coumarin derivatives.
Cinchona-based squaramide-catalysed cascade aza-Michael-Michael addition: Enantioselective construction of functionalized spirooxindole tetrahydroquinolines
Yang, Wen,Du, Da-Ming
, p. 8842 - 8844 (2013/09/24)
An efficient enantioselective cascade aza-Michael-Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 94% ee). The Royal Society of Chemistry 2013.
