13358-49-1Relevant articles and documents
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Kabuto,K. et al.
, p. 2357 - 2361 (1978)
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Studies directed toward the design of chiral acylating agents. the utility of chiral N-benzoylimides in enantioselective alcohol acylation
Evans, David A.,Anderson, James C.,Taylor, Marta K.
, p. 5563 - 5566 (1993)
N-benzoyl-4(5)-tert-butyl-2-oxazolidinone (1b) is found to be an efficient enantioselective acylating agent for aryl n-alkyl carbinols. Selective benzoylation of racemic aryl n-alkyl carbinols with kinetic selectivities of 20-30:1 for the (R) enantiomer i
Nucleophilic Substitution of (Alkoxymethylene)dimethylammonium Chloride with Carboxylate Salts: a Convenient Procedure for the Synthesis of Esters with Inversion of Configuration
Barrett, Anthony G. M.,Koike, Nobuyuki,Procopiou, Panayiotis A.
, p. 1403 - 1404 (1995)
Secondary alcohols are converted into benzoate esters with inversion of configuration via sequential reaction with (chloromethylene)dimethylammonium chloride and potassium benzoate.
Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols
Mayr, Stefanie,Marin-Luna, Marta,Zipse, Hendrik
, p. 3456 - 3489 (2021/03/01)
Relative rates for the Lewis base-mediated acylation of secondary and primary alcohols carrying large aromatic side chains with anhydrides differing in size and electronic structure have been measured. While primary alcohols react faster than secondary ones in transformations with monosubstituted benzoic anhydride derivatives, relative reactivities are inverted in reactions with sterically biased 1-naphthyl anhydrides. Further analysis of reaction rates shows that increasing substrate size leads to an actual acceleration of the acylation process, the effect being larger for secondary as compared to primary alcohols. Computational results indicate that acylation rates are guided by noncovalent interactions (NCIs) between the catalyst ring system and the DED substituents in the alcohol and anhydride reactants. Thereby stronger NCIs are formed for secondary alcohols than for primary alcohols.
Preparation of alkylated compounds using the trialkylphosphate
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Paragraph 0150-0151, (2021/11/02)
[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no