Stereoselective synthesis of novel beta,gamma-epoxyhydroxylamines and 4-hydroxyalkyl-1,2-oxazetidines

A simple and efficient stereoselective synthesis of polysubstituted beta,gamma-epoxyhydroxylamines and 4-hydroxyalkyl-1,2-oxazetidines, based on the addition of alpha-lithiated aryloxiranes to nitrones and subsequent cyclization of the corresponding intermediates in a 4-exo-tet mode, is described.     

Michael addition of ortho-lithiated aryloxiranes to alpha,beta-unsaturated malonates: synthesis of tetrahydroindenofuranones

A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described. The methodology has been applied to the synthesis of a structural analogue of epipodophyllotoxins.     

Regio- and stereoselective lithiation of 2,3-diphenylaziridines: a multinuclear NMR investigation

The alpha-lithiation-trapping sequence of trans-N-alkyl-2,3-diphenylaziridines (s-BuLi or s-BuLi/TMEDA), taking place with a stereochemistry which dramatically depends on the solvent coordinating ability (inversion of configuration in THF and retention in toluene), has been carefully investigated. 1H,13C, and 7Li multinuclear NMR investigations at low temperature suggest that two differently configured lithiated aziridines (monomeric cis-1-Li in THF and dimeric trans-1-Li in toluene) are involved.     

Regio- and stereoselective lithiation and electrophilic substitution reactions of N-Alkyl-2,3-diphenylaziridines: solvent effect

[structure: see text]. The lithiation reaction of cis- and trans-N-alkyl-2,3-diphenylaziridines has been investigated. While cis-diphenylaziridines do not undergo any lithiation upon treatment with organolithiums, the lithiation reaction of the trans counterparts is completely alpha-regioselective and the stereochemical course of the lithiation-trapping sequence is solvent dependent: inversion of configuration in coordinating solvents (THF or toluene/crown ether) and retention in hexane, ether, or toluene. The preparation of stereodefined functionalized N-alkyl-2,3-diphenylaziridines is described.     

Coherent Superpositions of Photon Creation Operations and Their Application to Multimode States of Light

We present a concise review of recent experimental results concerning the conditional implementation of coherent superpositions of single-photon additions onto distinct field modes. Such a basic operation is seen to give rise to a wealth of interesting and useful effects, from the generation of a tunable degree of entanglement to the birth of peculiar correlations in the photon numbers and the quadratures of multimode, multiphoton, states of light. The experimental investigation of these properties will have an impact both on fundamental studies concerning, for example, the quantumness and entanglement of macroscopic states, and for possible applications in the realm of quantum-enhanced technologies.     

Synthesis of 1,3-dihydrobenzo[c]furans from ortho-lithiated aryloxiranes

A general method for the synthesis of hydroxyalkyl 1,3-dihydrobenzo[c]furans from ortho-lithiated aryloxiranes and carbonyl compounds is described.