53138-75-3Relevant academic research and scientific papers
Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides
Liu, Xin,Werner, Thomas
, p. 1096 - 1104 (2020/12/31)
Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).
Matrix metalloprotease inhibitors
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, (2012/01/30)
The present invention relates to compounds of Formula I: STR1 that are matrix metalloprotease inhibitors, pharmaceutical compositions containing them, methods for their use and methods of preparing these compounds.
Matrix metalloprotease inhibitors
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, (2008/06/13)
Compounds of the formula: wherein: n is0, 1 or 2; Y ishydroxy or XONH-, where X is hydrogen or lower alkyl; R1is hydrogen or lower alkyl; R2is hydrogen, lower alkyl, heteroalkyl, aryl, aralkyl, arylheteroalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroaralkyl, heteroarylheteroalkyl, heterocyclo, heterocylo-lower alkyl, heterocyclo-lower heteroalkyl or -NR6R7, wherein: R6is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl, aryl, heteroaryl and heteroaralkyl; R7is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, -C(O)R8, -C(O)NR8R9, -SO2NR8R9, -SO2R10, aryloxycarbonyl, or alkoxycarbonyl; or R6and R7together with the nitrogen atom to which they are attached represent a heterocyclo group; wherein R8and R9are independently hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl or heteroalkyl; and R10is lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heteroalkyl or heterocyclo; or R1and R2together with the carbon atom to which they are attached represent a cycloalkyl or heterocyclo group; R3ishydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heteroalkyl or lower alkoxy; R4ishydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl; or R2and R3together with the carbons to which they are attached represent a cycloalkyl or heterocyclo group; or R3and R4together with the carbon to which they are attached represent a cycloalkyl or heterocyclo group; and R5islower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl; or pharmaceutically acceptable salts or esters thereof exhibit useful pharmacological properties, in particular for use as matrix metalloprotease inhibitors, particularly for interstitial collagenases.
Synthesis of α-stannyl α,β-unsaturated carboxylic esters
Zapata, Antonio J.,Fortoul R., Corina,Acuna A., Carola
, p. 69 - 74 (2007/10/02)
A synthetic method for the preparation of α-stannyl α,β-unsaturated esters is described.The lithium enolate derived from tert-butyl α-(tri-n-butylstannyl)-α-(trimethylsilyl)acetate reacts with aldehydes to give moderate to good yields of α-stannylated products.The method is not applicable to enolizable ketones.
Carbonyl olefination with α-stannyl ester enolates: a new synthesis of α,β-unsaturated esters
Zapata, Antonio,Nunez, Beatriz M.,Ferrer, Fernando J.
, p. C9 - C11 (2007/10/02)
The reaction of α-stannyl ester enolates with carbonyl compounds is described. α,β-Unsaturated esters are obtained in good yields.A reaction mechanism is proposed.
Peterson Olefination Reaction Using (Trimethylgermyl)acetate. Stereoselective Synthesis of (E)-2-Alkenoic Acid Esters
Inoue, Sumie,Sato, Yoshiro
, p. 347 - 352 (2007/10/02)
Peterson-type reaction of (trimethylgermyl)acetates 1 with aldehydes and ketones 2 gave stereoselectively (E)-2-alkenoic acid esters (E)-4 after stirring at -78 deg C and warming to room temperature.High yields of the reaction intermediates threo- and erythro-3-hydroxy-2-(trimethylgermyl)alkanoic acid esters 3 were obtained when the reaction was quenched at -78 deg C.The paths for conversion of threo-3 and erythro-3 to (E)-4 are discussed.
