- A simple primary amine catalyst for enantioselective α-hydroxylations and α-fluorinations of branched aldehydes
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A new primary amine catalyst for the asymmetric α-hydroxylation and α-fluorination of α-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for α-functionalizations. Promising initial results in α-amination and α-chlorination reactions support this hypothesis.
- Witten, Michael R.,Jacobsen, Eric N.
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p. 2772 - 2775
(2015/06/16)
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- Resolution of diols via catalytic asymmetric acetalization
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A highly enantioselective kinetic resolution of diols via asymmetric acetalization has been achieved using a chiral confined imidodiphosphoric acid catalyst. The reaction is highly efficient for the resolution of tertiary alcohols, giving selectivity factors of up to >300. Remarkably, even in cases where the selectivity factors are only moderate, highly enantioenriched diols are obtained via a stereodivergent resolution to diastereomeric acetals.
- Kim, Ji Hye,ori, Ilija,Palumbo, Chiara,List, Benjamin
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p. 1778 - 1781
(2015/03/04)
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- Benzimidazolones: A new class of selective peroxisome proliferator- activated receptor γ (PPARγ) modulators
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A series of benzimidazolone carboxylic acids and oxazolidinediones were designed and synthesized in search of selective PPARγ modulators (SPPARγMs) as potential therapeutic agents for the treatment of type II diabetes mellitus (T2DM) with improved safety profiles relative to rosiglitazone and pioglitazone, the currently marketed PPARγ full agonist drugs. Structure-activity relationships of these potent and highly selective SPPARγMs were studied with a focus on their unique profiles as partial agonists or modulators. A variety of methods, such as X-ray crystallographic analysis, PPARγ transactivation coactivator profiling, gene expression profiling, and mutagenesis studies, were employed to reveal the differential interactions of these new analogues with PPARγ receptor in comparison to full agonists. In rodent models of T2DM, benzimidazolone analogues such as (5R)-5-(3-{[3-(5-methoxybenzisoxazol-3-yl)benzimidazol-1-yl]methyl}phenyl) -5-methylox-azolidinedione (51) demonstrated efficacy equivalent to that of rosiglitazone. Side effects, such as fluid retention and heart weight gain associated with PPARγ full agonists, were diminished with 51 in comparison to rosiglitazone based on studies in two independent animal models. (Figure presented)
- Liu, Weiguo,Lau, Fiona,Liu, Kun,Wood, Harold B.,Zhou, Gaochao,Chen, Yuli,Li, Ying,Akiyama, Taro E.,Castriota, Gino,Einstein, Monica,Wang, Chualin,McCann, Margaret E.,Doebber, Thomas W.,Wu, Margaret,Chang, Ching H.,McNamara, Lesley,McKeever, Brian,Mosley, Ralph T.,Berger, Joel P.,Meinke, Peter T.
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p. 8541 - 8554
(2012/02/04)
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- INDOLES HAVING ANTI-DIABETIC ACTIVITY
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Indoles of Formula (I) having -X-aryl-(CH2)x#191-oxazolidinedione and -X-heteroaryl-(CH2)X-oxazolidinedione substituents on the N atom of the indole ring, where x is 0 or 1, and -X-is a bond or -CH2-, and their thiazolidinedione analogs, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia, dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity that are often associated with type 2 diabetes.
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Page/Page column 45
(2008/06/13)
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- BENZOUREAS HAVING ANTI-DIABETIC ACTIVITY
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Benzourea compounds of Formula I having aryl-(CH2)x-oxazolidinedione or aryl-(CH2)x-thiazolidinedione substituents on one of the N atoms of the benzourea ring, wherein x is 0 or 1, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia and other symptoms such as dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity, that are often associated with type 2 diabetes. I
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Page/Page column 31
(2008/06/13)
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