29481-98-9Relevant academic research and scientific papers
Stereoselective aziridination of cyclic allylic alcohols using chloramine-T
Coote, Susannah C.,O'Brien, Peter,Whitwood, Adrian C.
supporting information; experimental part, p. 4299 - 4314 (2009/02/07)
The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC6H4SO 2NClNa, TsNClNa and t-BuSO2NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis-hydroxy aziridine, whilst complete cis- diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis-stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.
Oxidative Generation of 1-Nitroalkyl Radicals and Their Addition Reaction to Olefins
Arai, Noriyoshi,Narasaka, Koichi
, p. 2525 - 2534 (2007/10/03)
1-Nitroalkyl radicals are generated by oxidation of potassium salt of 1-aci-nitroalkanes with ammonium hexanitratocerate(IV). When the oxidation is carried out in the presence of electron-rich olefins, such as silyl enol ethers, intermolecular addition of the radicals onto the olefins proceeds to afford β-nitro ketones, which are further converted to α,β-unsaturated ketones in high yield. Stereoselective construction of fused ring systems is achieved by intramolecular addition of 1-nitroalkyl radicals.
Cyclohexane-based 1,3-Dipodands; Complexation and Conformational Biasing
Shirodkar, Shailaja M.,Weisman, Gary R.
, p. 236 - 238 (2007/10/02)
Cyclohexane-based cis-1,3-dipodand (1) undergoes ring inversion to a diaxial conformation upon Na(1+) complexation, while related diaxially biased dipodand (2) is a better host.
Regioselective Synthesis of Substituted Bicyclooct-3-ene-2,8-diones via Double Carbonylation of 1,3-Cyclohexadienes
Eilbracht, Peter,Jelitte, Ruediger,Trabold, Peter
, p. 169 - 181 (2007/10/02)
Double carbonylation of 1,3-cyclohexadienes 1 is applied to the synthesis of substituted bicyclooct-3-ene-2,8-diones 4.The Lewis acid mediated ring enlargement of substituted cyclohexadiene complexes 2 produces the cycloheptanone alkyl allyl complexes 3 with high regioselectivity.Substituted bicyclic diketones 4 are obtained in high yields by treating the complexes 3 with carbon monoxide under pressure or by oxidative decomposition.The two carbonylation steps can also be performed in a one-pot version.
SYNTHESIS WITH ORGANOBORANES. 2. SYNTHESIS OF α- AND γ-DAMASCONE
Zaidlewicz, Marek
, p. 5135 - 5138 (2007/10/02)
Selective synthesis of α- and γ-damascone, using allylic organoboranes as key intermediates, are described.
