365441-85-6Relevant articles and documents
Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy
Willumstad, Thomas P.,Boudreau, Paul D.,Danheiser, Rick L.
, p. 11794 - 11805 (2015)
A two-stage "tandem strategy" for the regiocontrolled synthesis of very highly substituted quinolines is described. Benzannulation based on the reaction of cyclobutenones or diazo ketones with N-propargyl-substituted ynamides proceeds via a cascade of several pericyclic reactions to generate multiply substituted aniline derivatives. In the second stage of the tandem strategy, triflate derivatives of the phenolic benzannulation products undergo Larock cyclization upon exposure to iodine to form products that are further elaborated by methods such as palladium-catalyzed coupling to generate quinolines that can be substituted at every position of the bicyclic system.
Catalytic asymmetric Mannich reaction of glycine Schiff bases with α-amido sulfones as precursors of aliphatic imines
Hernando, Elier,Arrayas, Ramon Gomez,Carretero, Juan C.
supporting information, p. 9622 - 9624 (2012/11/07)
A general and practical CuI-Fesulphos-catalyzed Mannich reaction of glycinate Schiff bases with aliphatic imines generated in situ from α-amido sulfones is described. Imines with linear and branched alkyl chains, including substrates bearing functional groups, can be efficiently applied. The resulting syn-configured orthogonally protected β-alkyl-α,β-diamino acid derivatives are produced with excellent levels of diastereo- (typically syn/anti >90:10) and enantioselectivity (generally ≥90% ee).
Reductive BOC-amination of aldehydes
Bernacka, Elbieta,Klepacz, Anna,Zwierzak, Andrzej
, p. 5093 - 5094 (2007/10/03)
Base-assisted elimination-reduction of α-amidoalkyl sulfones with sodium borohydride proceeds in tetrahydrofuran at room temperature leading to the corresponding BOC-amines in good yields.
