- Diastereoselective Synthesis of Cyclic sp 3 -Enriched cis -β-Alkoxysulfonyl Chlorides
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A three-step synthesis of β-alkoxy-substituted alicyclic sulfonyl chlorides from cyclic alkenes and alcohols is reported. The scope of the method was studied for a range of the substrates with various steric and electronic properties. The title compounds were obtained on a hundred-gram scale in up to 52% overall yield scale as single cis -diastereomers.
- Sokolov, Andriy,Golovach, Sergey,Kozlinsky, Ihor,Dolia, Krystyna,Tolmachev, Andrey A.,Kuchkovska, Yuliya,Grygorenko, Oleksandr O.
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supporting information
p. 848 - 858
(2019/02/10)
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- A useful propionate cofactor enhancing activity for organic solvent-tolerant recombinant metal-free bromoperoxidase (perhydrolase) from Streptomyces aureofaciens
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The oxidative brominating activity of an organic solvent-tolerant recombinant metal-free bromoperoxidase BPO-A1 with C-terminal His-tag (rBPO-A1), from Streptomyces aureofaciens found to depend on various additives. These included carboxylic acids, used as cofactors and alcohols, used as water-miscible organic solvents. Enzyme activity was significantly enhanced by using propanoic acid (PA) as a cofactor, which had a high Log D at pH 5.0 and ethylene glycol with a low Log P. The positional specificity of oxidative hydroxybromination for olefins, using rBPO-A1 and PA in the presence of methanol, was higher compared to a non-enzymatic reaction using peracetic acid. The oxidative bromination step, occurring after enzymatic peroxidation step, is suggested to be pseudoenzymatic.
- China, Hideyasu,Ogino, Hiroyasu
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p. 327 - 332
(2019/07/12)
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- BNBTS More than brominating agent: Green and one-pot route for the C-N bond formation in water from alkenes
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In this paper, in addition to introducing efficient method for bromohydrin and bromoether preparation, simple, green and efficient method to C-N bond formation from alkene and N,N'-Dibromo-N,N'-1,2-ethanediyl- bis(ptoluenesulfonamide) [BNBTS] in water was investigated. The reaction between alkenes, β-cyclodexterin, and BNBTS took place in water afterward, by making media basic; it will give the corresponding valuable building blocks in good yields (45-79%).
- Kazemi, Foad,Kakroudi, Mazaher Abdollahi
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p. 500 - 504
(2013/08/25)
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- Alkoxybromination of olefins using ammonium bromide and oxone
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A mild, efficient, and highly regio- and stereoselective method for the methoxy and ethoxy bromination of olefins has been developed using NH 4Br as a bromine source and Oxone as an oxidant. Various kinds of olefins (aromatic, linear, and cyclic olefins) afforded the corresponding alkoxy brominated products in moderate to excellent yields. Taylor & Francis Group, LLC.
- Kumar, Macharla Arun,Naresh, Mameda,Rohitha, Chozhiyath Nappunni,Narender, Nama
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supporting information
p. 3121 - 3129
(2014/01/06)
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- Organocatalysis in the stereoselective bromohydrin reaction of alkenes
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An efficient regio- and stereo-selective (>99:1) trans-bromohydrination (bromohydroxylation and bromomethoxylation) of alkenes including α,β-unsaturated carbonyl compounds with N-bromosuccinimide (NBS) has been achieved by using 1.0 mol% of N,N'-diarylthi
- Bar, Sukanta
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experimental part
p. 605 - 612
(2010/08/21)
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- Functionalisation of indene
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Dibromo- and tribromoindane were synthesised by bromination of indene. Treatment of dibromo- and tribromoindane with various silver salts (silver acetate, perchlorate, sulfate and nitrate) in different solvents opened up an entry to the synthesis of various di- and tri-substituted indane derivatives.
- Tutar, Ahmet,Cakmak, Osman,Balci, Metin
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p. 507 - 511
(2007/10/03)
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- Electrophilic Additions to Indene and Indenone: Factors Effecting Syn Addition
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The electrophiles bromine, bromine chloride, chlorine, acetyl hypochlorite, and acetyl hypobromite all yield substantial cis addition product by reaction with indene (1) in aprotic solvents, showing that the direct syn collapse of ion pairs obtained from bromine and similar electrophiles is readily possible.The cis to trans ratios with the halogens (but not with the acyl hypohalites) vary with solvent polarities.In the low-polarity solvents (hydrocarbons and carbon tetrachloride) much more syn addition occurs at high halogen concentration.Syn addition of the above electrophiles to 1 as well as methyl hypobromite and methyl hypochlorite was also observed in methanol and acetic acid, with the exception of bromination in methanol where only the trans-dibromide was obtained.Bromine and bromine chloride addition to indenone (20) yielded only the trans-dihalides, suggesting that a neighboring keto group stabilizes the bridged bromonium ion.Chlorination of 20 was not stereospecific but yielded more trans-dichloride than did chlorination of 1.
- Heasley, Gene E.,Bower, Timothy R.,Dougharty, Kent W.,Easdon, Jerome C.,Heasley, Victor L.,et al.
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p. 5150 - 5155
(2007/10/02)
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