- Di[(R)-2-ethylhexyl] phthalate, a bioactive metabolite first isolated from three different bacillus species, and its synthesis
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Di(2-ethylhexyl) phthalate (DEHP) is the most common phthalate ester, which has been used as a plasticizer for the production of numerous polymers, particularly polyvinyl chloride (PVC). Many other groups have synthesized meso-DEHP indicating interest in this molecule, but we are the first to synthesize enantiomerically pure di[(R)-2-ethylhexyl] phthalate. We report herein, for the first time, the isolation-from the cultures of Bacillus thuringiensis, B. subtilis, and B. velezensis strains-of di[(R)-2-ethylhexyl] phthalate, enantiomerically pure and in good yields: its biological activity against bacteria and fungi was probed and for the first time its synthesis was done.
- Castro, Miriam,Jiménez, Jacqueline,Ortiz, Aurelio,Sansinenea, Estibaliz
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- Catalytic, enantioselective N-acylation of lactams and thiolactams using amidine-based catalysts
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In contrast to alcohols and amines, racemic lactams and thiolactams cannot be resolved directly via enzymatic acylation or classical resolution. Asymmetric N-acylation promoted by amidine-based catalysts, particularly Cl-PIQ 2 and BTM 3, provides a convenient method for the kinetic resolution of these valuable compounds and often achieves excellent levels of enantioselectivity in this process. Density functional theory calculations indicate that the reaction occurs via N-acylation of the lactim tautomer and that cation-π interactions play a key role in the chiral recognition of lactam substrates.
- Yang, Xing,Bumbu, Valentina D.,Liu, Peng,Li, Ximin,Jiang, Hui,Uffman, Eric W.,Guo, Lei,Zhang, Wei,Jiang, Xuntian,Houk,Birman, Vladimir B.
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supporting information
p. 17605 - 17612
(2013/01/15)
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- Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation
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Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities. Copyright
- Birman, Vladimir B.,Jiang, Hui,Li, Ximin,Guo, Lei,Uffman, Eric W.
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p. 6536 - 6537
(2007/10/03)
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- Stereoselective gram-scale synthesis of (S)-5,5-dimethyl-4-phenyloxazolidin-2-one
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A stereoselective gram-scale synthesis of (S)-5,5-dimethyl-4-phenyloxazolidin-2-one, SuperQuat [(S)-1], is described. The key step is the diastereoselective reduction of (E)-imine (2), which is synthesized from 2-hydroxy-2-methylpropiophenone (4) and (S)-
- Sugiyama, Shigeo,Arai, Satoshi,Ishii, Keitaro
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p. 149 - 159
(2007/10/03)
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- The 'SuperQuat' (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effective chiral auxiliary for conjugate additions: Asymmetric synthesis of (-)-aplysillamide B.
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(R)-4-Phenyl-5,5-dimethyl-oxazolidin-2-one, readily available from D- phenylglycine, is shown to be an effective chiral auxiliary for stereoselective conjugate additions to attached α,β-unsaturated N-acyl moieties. Its utility is demonstrated by the asymmetric synthesis of the antifungal, antibacterial (-)-Aplysillamide B.
- Davies, Stephen G.,Sanganee, Hitesh J.,Szolcsanyi, Peter
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p. 3337 - 3354
(2007/10/03)
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- Asymmetric alkylations using SuperQuat auxiliaries - An investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones
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Studies on the alkylation of enolates derived from a range of N-acyl-5,5-dimethyloxazolidin-2-ones and N-acyl-5,5-diphenyloxazolidin-2-ones reveal that high yields and high diastereoselectivities are best obtained when homochiral 4-isopropyl-5,5-dimethyloxazolidin-2-one is employed as a chiral auxiliary.
- Bull, Steven D.,Davies, Stephen G.,Jones, Simon,Sanganee, Hitesh J.
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p. 387 - 398
(2007/10/03)
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- Chiral auxiliaries
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This invention relates to novel compounds of general formula (I): STR1 wherein the two R1 groups are identical lower alkyl groups or together form a lower alkylene group; R2 and R3 are both different and are selected from hydrogen atoms or organic groups; X and X', which may be the same or different, are selected from O, S and NR, where R represents an organic group; and the asterisk denotes that the configurations of R2 and R3 are such that the compound (I) is in substantially enantiomerically pure 4R- or 4S-form. The compounds are useful chiral auxiliaries to which a wide range of, for example, acyl groups containing prochiral centers may be readily and reversibly coupled to the 3-position amino group.
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