Immobilization of cis‐4‐Hydroxydiphenylprolinol Silyl Ethers onto Polystyrene. Application in the Catalytic Enantioselective Synthesis of 5‐Hydroxyisoxazolidines in Batch and Flow. Issue 15 (22nd June 2018)

• Record Type: Journal Article
• Authors: Lai, Junshan; Sayalero, Sonia; Ferrali, Alessandro; Osorio‐Planes, Laura; Bravo, Fernando; Rodríguez‐Escrich, Carles; Pericàs, Miquel A.
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 15(2018)
• Page Start: 2914
• Page End: 2924
• Publication Date: 2018-06-22
• Subjects: supported catalysts -- organic catalysis -- flow chemistry -- asymmetric catalysis -- isoxazolidines; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201800572
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A new family of polystyrene‐supported cis ‐4‐hydroxydiphenylprolinol silyl ethers has been prepared, and the resulting polymers have been evaluated as organocatalysts to promote the tandem reaction between N ‐protected hydroxylamines and α, β‐unsaturated aldehydes in batch and flow. The new PS‐supported catalysts compare favorably with well‐established immobilized Jørgensen‐Hayashi catalysts, affording 5‐hydroxyisoxazolidines as single diastereoisomers with high enantioselectivities and good yields (up to 83% yield, up to 99% ee). Abstract :