76287-54-2Relevant articles and documents
Highly enantioselective dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipoprotein lipase preparation
Cho, Jeonghun,Lee, Jusuk,Park, Jaiwook,Kim, Mahn-Joo
, p. 840 - 845 (2015/08/18)
Abstract The kinetic and dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipase preparation containing lipoprotein lipase, dextrin, and ionic surfactant 1 has been explored. It was found that all the trimethylsilyl-containing substrates were accepted by lipoprotein lipase-dextrin 1 (LPL-D1) with perfect enantioselectivity (E = >200). As a result, the dynamic kinetic resolution of these substrates with LPL-D1 in the presence of a Ru-based racemization catalyst provided single enantiomeric products (>99% ee) with good yields. Furthermore, the dynamic kinetic resolution products were readily desilylated or halodesilylated to yield enantiopure alkyl aryl carbinols. Thus a useful protocol for the highly enantioselective synthesis of alkyl aryl carbinols, particularly those carrying a long alkyl chain (C6-C10) has been established.
Catalytic asymmetric addition of alkyllithium reagents to aromatic aldehydes
Fernandez-Mateos, Emilio,MacIa, Beatriz,Yus, Miguel
supporting information; body text, p. 3732 - 3736 (2012/09/21)
Herein, we report the first efficient catalytic system for the asymmetric alkylation of aldehydes with organolithium reagents in the presence of titanium(IV) isopropoxide. A variety of alkyllithium reagents can be added to aromatic aldehydes in good yields with high enantioselectivities in a simple one-pot procedure under mild conditions. Herein, we report the first efficient catalytic system for the asymmetric alkylation ofaldehydes with organolithium reagents in the presence of titanium(IV) isopropoxide. A variety of alkyllithium reagents can be added to aromatic aldehydes in good yields with high enantioselectivities in a simple one-pot procedure under mild conditions. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
A novel one-pot synthesis of secondary alcohols from esters
Chae, Min Jung,Jeon, Ah Ram,Park, Jae Kyo,An, Duk Keun
experimental part, p. 1718 - 1720 (2011/04/25)
Alkylation or vinylation by using organometallic reagents after partial reduction of carboxylic esters with LDBBA gave secondary alcohols, also involving allyl alcohols, without any isolation of intermediates in good yield (54-78%).
INHIBITORS OF DIACYLGLYCEROL O-ACYLTRANSFERASE TYPE 1 ENZYME
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Page/Page column 63-64, (2008/12/08)
The present invention relates to compounds of formula (I): wherein Q, G1, G2, and G3, are defined herein. Pharmaceutical compositions and methods for treating DGAT-1 related diseases or conditions are also disclosed.
Syntheses with organoboranes. XIII. Synthesis of ω-(4-bromophenyl)alkanoic acids and their borylation
Zaidlewicz, Marek,Wolan, Andrzej
, p. 129 - 135 (2007/10/03)
ω-(4-Bromophenyl)alkanoic acids 2c-e were obtained from 1-bromo-4-alkenylbenzenes 5c-e by hydroboration-thermal isomerization-oxidation. Their esters 11c-e were transformed in good yields into the corresponding boronates 12c-e by the cross-coupling reaction with (10) in an ionic liquid, [bmim][BF4]. The use of pinacolborane for the coupling reaction in the ionic liquid gave debromination products, and low yields of 12c-e. Ethyl 3-(4-bromophenyl)propanoate (7c) was transformed into ethyl 3-(4-[1,3,2]dioxaborolanyl)propanoate (9c) by the cross-coupling with [2,2′]bi[[1,3,2]dioxaborinanyl].
Alkylation of aromatic aldehydes with alkylboron chloride derivatives
Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong
, p. 1663 - 1670 (2007/10/03)
The reaction of aryl aldehydes with alkylboron chlorides has been investigated. Monoalkylboron dichlorides react with aryl aldehydes in hexane under reflux conditions to give a mixture of dichloroarylmethane and benzyl chloride. Under the same reaction conditions, dialkylboron chlorides lead to formation of a mixture of benzyl chloride and the chloroalkylation product. In the presence of a base such as 2,6-lutidine, the reactions of monoalkylboron dichlorides with aryl aldehydes yield small amounts of the desired alkylation products at room temperature. Dialkylboron chlorides react with aryl aldehydes in hexane in the presence of base to generate the corresponding arylalkylmethanols in good yields.
Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes
Kabalka, George W.,Maddox, John T.,Bogas, Ekaterini,Kelley, Shane W.
, p. 3688 - 3695 (2007/10/03)
(Arenesulfonyl)hydrazone derivatives of aryl aldehydes are readily alkylated by trialkylboranes in the presence of base to generate new organoboranes that may be converted to the corresponding substituted alkanes or alcohols depending upon the reaction conditions chosen. Both tosyl- and trisylhydrazone derivatives can be utilized in the reaction, which tolerates a variety of functional groups, making it a versatile alternative to both the Grignard and Suzuki-coupling reactions.
A facile alkylation of aryl aldehyde trisylhydrazones with trialkylboranes
Kabalka, George W.,Maddox, John T.,Bogas, Ekaterini,Tejedor, David,Ross, Emily J.
, p. 999 - 1006 (2007/10/03)
Tributylborane readily alkylates aryl aldehyde trisylhydrazones to produce the corresponding alcohols in excellent yields.
A Facile Alkylation of Aryl Aldehyde Tosylhydrazone with Trialkylboranes
Kabalka, George W.,Maddox, John T.,Bogas, Ekaterini
, p. 5530 - 5531 (2007/10/02)
Trialkylboranes readily alkylate aryl aldehyde tosylhydrazones to produce either the corresponding arylalkane or aryl alcohol in excellent yields.
Formation of Secondary Alcohols from the Reaction of Trimethyl- and Methyldiphenyl-telluronium Salts with Aldehydes by Use of Organolithium Reagents
Shi, Li-Lan,Zhou, Zhang-Lin,Huang, Yao-Zeng
, p. 2847 - 2848 (2007/10/02)
The telluronium salts (1) and (2), precursors of the non-stabilized telluronium ylide, on treatment with organolithium reagents, reacted with aldehydes to afford secondary alcohols via tetraorganyl tellurium intermediates.
