- Regio- and chemoselective rearrangement of terminal epoxides into methyl alkyl and aryl ketones
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The development of the highly active pincer-type rhodium catalyst 2 for the nucleophilic Meinwald rearrangement of functionalised terminal epoxides into methyl ketones under mild conditions is presented. An excellent regio- and chemoselectivity is obtained for the first time for aryl oxiranes.
- Tian, Yingying,Jürgens, Eva,Kunz, Doris
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supporting information
p. 11340 - 11343
(2018/10/31)
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- Novel synthesis and enzymatic resolution of (±)-2,3-epoxy propyl esters
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A novel method of synthesizing glycidyl esters (±) -2,3-epoxy propyl esters has been developed involving reaction of epichlorohydrin with sodium salt of carboxylic acids in the presence of 15-crown-5 as catalyst with excellent yields. Enzymatic resolution of these glycidyl esters by lipasePS- C has been achieved with remarkable substrate selectivity.
- Nair, Ranjeet V.,Patil, Prashant N.,Salunkhe, Manikrao M.
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p. 2559 - 2566
(2007/10/03)
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- Role of the (Acyloxy)methyl Moiety in Eliciting the Adrenergic β-Blocking Activity of 3-(Acyloxy)propanolamines
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Some totally aliphatic 3-(acyloxy)propanolamines were synthesized with the aim of testing whether β-blocking activity could be obtained from this class of drugs, even in the absence of an aromatic group.The significant and, in most cases, competitive β-blocking activity shown by the compounds under examination, together with the results of a theoretical study in which their reactivity was compared with that of other adrenergic β-blocking drugs, seems to confirm a hypothesis previously advanced on the basis of knowledge about the action mechanism of adrenergic β-blocking drugs and of the results of structural studies.It was also possible to suggest some considerations about the role played by the (acyloxy)methyl portion of 3-(acyloxy)propanolamines in eliciting their adrenergic β-blocking activity.
- Macchia, B.,Balsamo, A.,Lapucci, A.,Macchia, F.,Martinelli, A.,et al.
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p. 616 - 622
(2007/10/02)
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- SELECTIVE REDUCTION OF α,β-UNSATURATED ESTERS IN THE PRESENCE OF OLEFINS
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Several α,β-unsaturated esters containing also isolated olefins or other functionalities subject to saturation were selectively reduced to the corresponding saturated esters by magnesium in methanol.
- Hudlicky, T.,Sinai-Zingde, G.,Natchus, M. G.
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p. 5287 - 5290
(2007/10/02)
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- A Convenient Synthesis of Glycidyl Esters (2,3-Epoxypropyl Alkanoates)
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A novel method for synthesizing glycidyl esters (2,3-epoxypropyl alkanoates) 1 has been achieved by the sequence of the organotin phosphate catalyzed reaction of epichlorohydrin 2 with carboxylic acids and dehydrochlorination of the resulting mixture of ester chlorohydrins 3 + 4 followed by separation.
- Otera, Junzo,Matsuzaki, Shinjiro
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p. 1019 - 1020
(2007/10/02)
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- An Electron Spin Resonance Study of 3-Oxypropenoyl Radicals derived from Glycidols
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Glycidols with blocked OH groups (A; M = alkyl or trialkylsilyl) react with t-butoxyl radicals to show the e.s.r. spectra of the corresponding 3-oxypropenoyl radicals (D), and 24 examples of these acyl radicals are reported.The reaction is thought to proceed through the formation of the allyloxyl radicals (B), which, in part, are converted into the aldehyde (C) which is very reactive towards loss of hydrogen to give the acyl radical (D).Glycidyl pivalate (A; M = COCMe3) reacts cleanly in this way, but glycidyl acetate (E; R = Me) also undergoes intramolecular 1,5-transfer of the acyl group to show the spectrum of the enoxyl radical (F).Glycidyl propionate and butyrate do not undergo this acyl transfer, but show the spectra of the radicals and (R' = Me or Et).
- Davies, Alwyn G.,Hawari, Jalal A.-A.,Muggleton, Brenda,Tse, Man-Wing
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p. 1132 - 1137
(2007/10/02)
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