13892-06-3Relevant articles and documents
A Scalable Total Synthesis of (-)-Nakadomarin A
Boeckman, Robert K.,Wang, Hui,Rugg, Kyle W.,Genung, Nathan E.,Chen, Ke,Ryder, Todd R.
, p. 6136 - 6139 (2016)
The convergent total synthesis of the manzamine alkaloid (-)-nakadomarin A (1) is described. The retrosynthetic analysis recognized spirocycle 3, assembled via an organocatalyst-promoted Michael addition/cyclization between bicyclic lactam 4 and furan ald
Iminophosphoranyl dichlorophosphines R3PNPCl2
Eckart, Andreas,Lux, Karin,Karaghiosoff, Konstantin
, p. 962 - 967 (2014/04/17)
The iminophosphoranyl dichlorophosphines Ph3PNPCl2 (2a), pTol3PNPCl2 (2b), and Cy3PNPCl 2 (2c) were synthesized by reaction of trimethylsilyliminophosphoranes R3PNSiMe3/sub
Synthetic and mechanistic studies of the aza-retro-claisen rearrangement. a facile route to medium ring nitrogen heterocycles
Boeckman Jr., Robert K.,Genung, Nathan E.,Chen, Ke,Ryder, Todd R.
supporting information; experimental part, p. 1628 - 1631 (2010/06/19)
An efficient synthesis of medium-sized heterocyclic rings was achieved using a one-pot aza-Wittig/retro-aza-Claisen sequence of vinyl cyclobutanecarboxaldehydes derived from simple allylic carbonates. The use of various Staudinger reagents in the aza-Wittig reaction allows for a variety of N-substituted products to be obtained. The rearrangement is under thermodynamic control driven by relief of the cyclobutane ring strain and resonance stabilization of the resulting vinylogous amide/sulfonamide.
A one-pot aza-Wittig based solution and polymer supported route to amines
Hemming,Bevan,Loukou,Patel,Renaudeau
, p. 1565 - 1568 (2007/10/03)
This paper presents a high yielding one-pot solution phase and polymer supported synthesis of a range of primary and secondary amines starting from azides and aldehydes. The synthesis utilises a tandem process which begins with an aza-Wittig reaction between the aldehyde and an iminophosphorane, followed by reduction, or organometallic 1,2-addition reaction, of the resultant imine. The requisite iminophosphoranes were accessed using the highly efficient Staudinger reaction between the azide starting material and a phosphine. The process was applicable to the solid phase by the use of polymer supported iminophosphoranes and polymer supported cyanoborohydride.
New versatile fluorinated chiral building blocks: Synthesis and reactivity of optically pure α-(fluoroalkyl)-β-sulfinylenamines
Arnone, Alberto,Bravo, Pierfrancesco,Capelli, Silvia,Fronza, Giovanni,Meille, Stefano V.,Zanda, Matteo,Cavicchio, Giancarlo,Crucianelli, Marcello
, p. 3375 - 3387 (2007/10/03)
Efficient synthesis of optically pure α-(fluoroalkyl)-β-sulfinyl enamines has been achieved by aza-Wittig reaction of triphenyliminophosphoranes with the corresponding α-fluorinated-α'-sulfinyl ketones. The title compounds 3,4 showed an overwhelming prefe
Synthesis and characterisation of new bis(pentadienylium) cations with 1,4-phenylenediamine spacer
Saggio, Guillaume,Mazieres, Marie-Rose,Fialon, Marie-Pierre,Sanchez, Michel,Wolf, Jean-Gerard
, p. 1071 - 1080 (2007/10/03)
The chemistry of the carboxonium salts and their mono-substituted derivatives has been investigated.Their reactivity towards bifunctional spacers like 1,4-phenylenediamine leads to bis-cationic cyanine dyes with an enhanced delocalization pathway and original optical properties.This molecular engineering may easily afford higher polycationic homologs. - Keywords: cyanine dye; conjugated dication; visible spectra; solvatochromism
PREPARATION OF DI- AND TRIACYLIMINES AND THEIR USE IN THE SYNTHESIS OF NITROGEN HETEROCYCLES
Jung, Michael E.,Shishido, Kozo,Light, Lynn,Davis, Leonard
, p. 4607 - 4610 (2007/10/02)
Reaction of aza-Wittig reagents with glyoxylates and keto malonates produces di- and triacylimines which are moderately reactive dienophiles for Diels-Alder cycloaddition.
Facile preparation of silyl azides with dipolar aprotic solvents
S. Washburne, Stephen,R. Peterson Jr., William
, p. 153 - 156 (2007/10/05)
The reaction of sodium azide with chlorosilanes in hexamethylphosphoric triamide or dimethylformamide at room temperature affords a high yield preparation of silyl azides, e.g. Me3SiN3,Me2Si(N3)2, PhMeSi(N3)2 and Ph2Si(N3)2. For characterization, the azides may be converted to silyphosphiimies, R3Si-N=PPh3.