Rapid stereoselective syntheses of heteroarene-fused azacycles via diastereoselective conjugate addition of heteroaryl substituted lithium amidest
Conjugate addition of heteroaryl substituted lithium amides to a range of α,β-unsaturated esters followed by in situ enolate oxidation with (-)-(camphorsulfonyl)oxaziridine gave the corresponding α-hydroxy-β-amino esters. Subsequent Friedel-Crafts type cy
Davies, Stephen G.,Fletcher, Ai M.,Holder, Katherine E.,Roberts, Paul M.,Thomson, James E.,Zimmer, David
p. 919 - 941
(2019/08/01)
Metal Acetylide Elimination: The Key Step in the Cascade Decomposition and Transformation of Metalated Propargylamines
Metal acetylide elimination facilitates a novel one-pot cascade metalation and elimination/addition route to a series of unsymmetrical secondary amines from the reaction of secondary propargylamines with organometallic reagents. Spectroscopic evidence suggests a dimetalated amido intermediate rather than an allene.
Flynn, Matthew T.,Blair, Victoria L.,Andrews, Philip C.
p. 1225 - 1228
(2018/04/30)
Asymmetric Imine Hydroboration Catalyzed by Chiral Diazaphospholenes
The first use of diazaphospholenes as chiral catalysts has been demonstrated with enantioselective imine hydroboration. A chiral diazaphospholene prepared in a simple three-step synthesis from commercial materials has been shown to achieve the highest enantioselectivity for the hydroboration of alkyl imines with pinacolborane reported to date. Enantiomer ratios of up to 88:12 were obtained with low (2 mol %) catalyst loadings. Twenty examples of asymmetric reduction employing this main-group catalysis protocol, including the synthesis of the pharmaceuticals ent-rasagiline and fendiline, are shown.
Adams, Matt R.,Tien, Chieh-Hung,McDonald, Robert,Speed, Alexander W. H.
supporting information
p. 16660 - 16663
(2017/12/13)
Iridium-catalysed amine alkylation with alcohols in water
Amines have been directly alkylated with alcohols using 1 mol% [Cp*IrI2]2 catalyst in water in the absence of base or other additives. The Royal Society of Chemistry 2010.
Saidi, Ourida,Blacker, A. John,Farah, Mohamed M.,Marsden, Stephen P.,Williams, Jonathan M. J.
supporting information; experimental part
p. 1541 - 1543
(2010/06/12)
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