50683-32-4Relevant articles and documents
Carbohydrate-derived iminium salt organocatalysts for the asymmetric epoxidation of alkenes
Bulman Page, Philip C.,Chan, Yohan,Liddle, John,Elsegood, Mark R.J.
, p. 7283 - 7305 (2017/09/13)
A new family of carbohydrate-based dihydroisoquinolinium salts has been prepared and tested for potential as asymmetric catalysts for the epoxidation of unfunctionalized alkene substrates, providing up to 57% ee in the product epoxides.
Cascade condensation, cyclization, intermolecular dipolar cycloaddition by multi-component coupling and application to a synthesis of (±)-crispine A
Coldham, Iain,Jana, Samaresh,Watson, Luke,Martin, Nathaniel G.
scheme or table, p. 1674 - 1679 (2009/06/27)
A general approach for the synthesis of various nitrogen-containing heterocyclic compounds is described using an intermolecular dipolar cycloaddition reaction of azomethine ylides and nitrones. Stabilized and non-stabilized azomethine ylide dipoles or the related nitrones were generated by condensation of 4-, 5- or 6-halo-aldehydes with a readily available amino-acid, amino-ester or hydroxylamine to give an imine followed by cyclization and either decarboxylation or loss of a proton. After intermolecular cycloaddition with an activated dipolarophile, bicyclic or polycyclic (if the ylide dipole and/or dipolarophile contain a ring) amines were produced. A short synthesis of the alkaloid (±)-crispine A was achieved based on this tandem/domino 3-component coupling chemistry.
Functionalized iminium salt systems for catalytic asymmetric epoxidation
Page,Rassias,Barros,Ardakani,Buckley,Bethell,Smith,Slawin
, p. 6926 - 6931 (2007/10/03)
A range of dihydroisoquinolinium salts containing alcohol, ether, and acetal functionalities in the nitrogen substituent has been prepared and tested as asymmetric epoxidation catalysts, providing ee's of up to ca. 60%.