The unimolecular photochemistry of 3,5-dimethylisoxazole (1) induced by a narrow-band tunable UV laser was studied using low-temperature matrix isolation coupled with infrared spectroscopy. Monomers of 1 were isolated in argon matrices at 15 K and characterized spectroscopically. Irradiation of matrix-isolated 1 at λ = 222 nm (near its absorption maximum) led to the corresponding 2H-azirine 3 a...

An ammonium ylide-mediated stereoselective protocol for the synthesis of a series novel [2.2]paracyclophane-based epoxides starting from racemic 4-formyl[2.2]paracyclophane has been developed. By using achiral salts as ylide precursors, corresponding epoxide products were obtained in isolated yields up to 76 % and with diastereoselectivities d.r.=9 : 1. When carrying out reaction chiral instead...

Article history: Received 13 April 2010 Accepted 28 April 2010 Available online 16 June 2010 Dedicated to Henri Kagan on the occasion of his 80th birthday 0957-4166/$ see front matter 2010 Elsevier Ltd. A doi:10.1016/j.tetasy.2010.04.046 * Corresponding author. Tel.: +44 117 954 6315; fa E-mail address: [email protected] (V.K. Agg The epoxidation of meroquinene aldehyde with a chiral sul...

Cycloaddition is a fundamental transformation, featuring the assembly of complex cyclic molecules with multiple stereocenters. We report here silver-catalyzed [3+2]-cycloaddition 2,3-disubstituted cyclobutenones an array azomethine ylide...

The total synthesis of the endogenous inflammation resolving eicosanoid resolvin D2 (1) is described. The key steps involved a Wittig reaction between aldehyde 5 and the ylide derived from phosphonium salt 6 to give enyne 17 and condensation of the same ylide with aldehyde 7 to afford enyne 11. Desilylation of 11 followed by hydrozirconation and iodination gave the vinyl iodide 4 and Sonogashir...

Tandem carbenoid generation, ylide formation and [2,3]-rearrangement is a powerful method for the construction of bicyclic and linearly fused tricyclic systems containing a seven-membered ring.

An asymmetric sulfur ylide reaction was employed to prepare an epoxide intermediate in a convergent manner. This epoxide was efficiently transformed into D-erythro-sphingosine.

A highly diastereoselective tandem ring-enlargement and aldol condensation process involving multicomponent reactions of ethereal tricyclooxonium ylide intermediate with alcohols, mono- or dialdehydes in the presence of titanium(iv) isopropoxide is described to furnish alkoxyoctahydro-1,4-benzodioxocin-6(5H)-one ring systems.