168985-70-4Relevant articles and documents
Overcoming equilibrium issues with carbonyl reductase enzymes
Calvin, Susan J.,Mangan, David,Miskelly, Iain,Moody, Thomas S.,Stevenson, Paul J.
experimental part, p. 82 - 86 (2012/05/31)
We report herein the screening, optimisation and scale up to 100 g of a bioreduction process that employs an in situ product removal (ISPR) technique to overcome the inherent equilibrium problem associated with the coupled-substrate approach to biocatalyt
Highly enantioselective and regioselective carbonyl reduction of cyclic α,β-unsaturated ketones using TarB-N02 and sodium borohydride
Kim, Jinsoo,Bruning, John,Park, Kevin E.,Lee, David J.,Singaram, Bakthan
supporting information; experimental part, p. 4358 - 4361 (2009/12/24)
Asymmetric 1,2-reduction of α,β-unsaturated ketones using TarB-NO2 and NaBH4 Is reported. Simple cycloalkenones give products In low enantiomeric excess. However, cycloalkenones with a-substituents, such as halides, alkyl, and aryl, have been enantioselectively reduced with this system to yield chiral allylic alcohols In enantiomeric excess up to 99%. The starting materials for TarB-N02 are inexpensive, and the boronlc acid can be easily recovered In high yield by a simple acid extraction.
A convenient halogenation of α,β-unsaturated carbonyl compounds with OXONE and hydrohalic acid (HBr,HCl)
Kim, Kyoung-Mahn,Park, In-Hwan
, p. 2641 - 2644 (2007/10/03)
Mixtures of OXONE and hydrobromic acid or hydrochloric acid afford solutions of bromine or chlorine, respectively, α-Bromo- or α-chloro-α,β-unsaturated carbonyl compounds were prepared by addition of hydrobromic acid or hydrochloric acid to the mixture of
Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp
Easton,Heath,Hughes,Lee,Savage,Simpson,Tiekink,Vuckovic,Webster
, p. 1168 - 1174 (2007/10/03)
Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N-O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.
Domino Michael-O-alkylation reaction: One-pot synthesis of 2,4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis
Hagiwara, Hisahiro,Sato, Kouji,Nishino, Daisuke,Hoshi, Takashi,Suzuki, Toshio,Ando, Masayoshi
, p. 2946 - 2957 (2007/10/03)
The one-pot synthesis of 2,4-diacylhydrofuran derivatives and its applications to antitumor napthofuran synthesis was discussed. It was found that the reaction of 1,3-dicarbonyl compounds with α-halo-α,β-unsaturated carbonyl compounds afforded 2,4-diacyldihydrofuran derivatives in the presence of DBU in THF. The analysis showed that the applications of the protocol enabled short-step synthesis of antitumor napthofuran natural products.
Trifluoromethanesulfonic anhydride-promoted α-bromination of ketones with Grignard reagent or magnesium bromide
Nishiyama,Ono,Kurokawa,Kimura
, p. 1999 - 2002 (2007/10/03)
The direct α-bromination of various ketones using trifluoromethanesulfonic anhydride and Grignard reagent or magnesium bromide in ether gave the corresponding α-bromo ketones in moderate to good yields under mild reaction conditions.
A radical based addition-elimination route for the preparation of indoles
Murphy, John A.,Scott, Karen A.,Sinclair, Rhoha S.,Martin, Concepcion Gonzalez,Kennedy, Alan R.,Lewis, Norman
, p. 2395 - 2408 (2007/10/03)
Indoles, including tricyclic derivatives, are produced by cyclisations of aryl radicals onto vinyl halides followed by elimination of halide radical and tautomerism of the resulting product; the aryl radicals are produced using "clean methodology" either by reaction of iodide ions with arenediazonium salts or by reaction of phosphorus-centred radicals with aryl iodides. The Royal Society of Chemistry 2000.
Oxidation of α,β-enones and alkenes with oxone and sodium halides: A convenient laboratory preparation of chlorine and bromine
Dieter, R. Karl,Nice, Lois E.,Velu, Sadanandan E.
, p. 2377 - 2380 (2007/10/03)
Mixtures of oxone and sodium chloride or sodium bromide afford solutions of chlorine or bromine, respectively. These solutions effectively add chlorine and bromine to α,β-enones and alkenes. The method affords improved yields of 3-alkyl-2-halo-2-cycloalkenones which are sometimes difficult to prepare.
The Diene-Transmissive -Cycloaddition Strategy: Stereoselective Synthesis of Advanced Intermediates to Quassinoids
Spino, Claude,Liu, Gang,Tu, Noah,Girard, Suzanne
, p. 5596 - 5608 (2007/10/02)
Complex intermediates to quassinoids, some optically active and containing many functional groups, were synthesized via a diene-transmissive Diels-Alder strategy.The stereochemistry of the key inter- and intramolecular cycloadditions was controlled by ste
α-Keto Dianion Precursors via Conjugate Additions to Cyclic α-Bromo Enones
Kowalski, Conrad J.,Weber, Ann E.,Fields, Kevin W.
, p. 5088 - 5093 (2007/10/02)
Successful conjugate to 2-bromocyclohexenone and 2-bromocyclopentenone have been achieved with a variety of lithium homocuprates, mixed cyanocuprates, and lithium tri-sec-butylborohydride as well.In all cases the resulting α-bromo enolate anions could be
