- β-siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions
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Double-action haloketones: A super silyl group enabled the first highly diastereoselective Mukaiyama aldol reactions of α-chloro- and α-fluoroketones with a wide range of aldehydes, providing anti-β-siloxy-α-haloketones. This process is compatible with one-pot double-aldol methodology and allows for rapid access to new halogen-modified polyketide fragments bearing up to four contiguous stereocenters (see scheme). Copyright
- Saadi, Jakub,Yamamoto, Hisashi
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supporting information
p. 3842 - 3845
(2013/04/24)
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- PRODUCTION OF 1,1,1-TRIHALOGENO-2-ALKANOLS AND SOME OF THEIR PROPERTIES
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The reaction of acyclic and carbocyclic carbonyl compounds with haloforms was studied in liquid ammonia and dimethylformamide in the presence of basic catalysts (t-BuOK, KOH).As a result of the reaction 1,1,1-trihalogeno-2-alkanols were obtained.They were used for the synthesis of 1,1,1-trihalogeno-2-methoxyalkanes, 1,1-dibromoalkenes, 1,1-dichloro-2-methoxyalkenes, and alkyl mono- and dichloromethyl ketones.
- Bal'on, Ya. G.,Shul'man, M. D.,Vakulenko, L. I.
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p. 1231 - 1237
(2007/10/02)
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- EINTOPFSYNTHESE TRICHLOROMETHYLSUBSTITUIERTER ALKOHOLE
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A new one-pot synthesis of alcohols RCH(OH)CCl3 starting from CCl4, Me3SiCl, Mg and aldehydes RCHO is described.
- Brunner, Henri,Wimmer, Peter
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- Lewis Acid Catalysis of Ene Addition of Chloral and Bromal to Olefins; Product Studies
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The addition of chloral and bromal to a variety of alkyl-substituted alkenes has been investigated.The effect of the reaction of varying the Lewis acid catalyst and the structure of substrate have been studied.Anhydrous AlCl3 was found to be most effective catalyst, and ene-type adducts were the major products in most cases.Side reactions were observed with the less reactive systems leading, variously, to the formation of trihalogenoketones, hydrohalogenated ene adducts, and cyclic ethers.Conditions for optimising the yield of ene adducts were established in some cases.The trihalogenoketone by-products can be conveniently removed by a Grignard-type reaction.
- Benner, Jill P.,Gill, G. Bryon,Parrott, Stephen J.,Wallace, Brian
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p. 291 - 313
(2007/10/02)
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- AN UNUSUAL REACTION OF TRICHLOROMETHANE WITH ACYLALS IN THE INTERPHASE CATALYSIS CONDITIONS.
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Aldehyde diacetates ract with trichloromethane in the standard interphase catalysis conditions to form α-trichloromethylcarbinols or their acetates depending on temperature and time of the reaction.
- Kryshtal, G. V.,Bogdanov, V. S.,Yanovskaya, L. A.
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p. 3607 - 3610
(2007/10/02)
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- NUCLEOPHILIC REACTIONS AT VINYL CENTER. V. SYNTHESIS OF α-METHYL-β,β-DICHLOROVINYL PHENYL SULFONE
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α-Methyl-β,β-dichlorovinyl phenyl sulfone was synthesized by the reaction of 1,1,2-trichloropropene with sodium thiophenolate in dimethylformamide and subsequent oxidation with hydrogen peroxide.The side reactions accompanying the formation of 1,1,2-trichloropropene during dehydration of 1,1,1-trichloro-2-propanol over phosphorus pentoxide were examined in detail.
- Shainyan, B. A.,Mirskova, A. N.
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