81418-17-9Relevant academic research and scientific papers
Application of a one-pot lipase resolution strategy for the synthesis of chiral γ- and δ-lactones
Kamal, Ahmed,Sandbhor, Mahendra,Shaik, Ahmad Ali
, p. 1575 - 1580 (2007/10/03)
A successful one-pot reduction of γ-ketoesters, δ-ketoesters and lactones to the corresponding 1,4- and 1,5-diols followed by a lipase catalyzed kinetic resolution coupled with hydrolysis to afford optically active diols is described. The synthetic utility of this one-pot method was illustrated by the oxidation of these chiral diols to respective chiral γ-butyrolactone and δ-lactones. Lipase from Pseudomonas cepacia, immobilized on ceramic afforded the product with high enantiomeric excess in good yields under mild reaction conditions. This approach has been used to develop a convenient enantioselective route for several γ- and δ-lactones using achiral and corresponding racemic starting material.
Inter- and intramolecular pathways for the formation of tetrahydrofurans from β-(phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism
Crich, David,Huang, Xianhai,Newcomb, Martin
, p. 523 - 529 (2007/10/03)
β-(Phosphatoxy)alkyl radicals generated by photolysis of Barton PTOC esters in the presence of allyl alcohol and tert-butyl mercaptan undergo nucleophilic substitution followed by 5-exo-trig radical ring closure leading to tetrahydrofurans in good yield and with high trans selectivity. β- (Phosphatoxy)alkyl radicals obtained by intramolecular hydrogen 1,5- abstraction with an alkoxyl radical undergo nucleophilic displacement providing tetrahydrofurans. The ensemble of results, including the effects of leaving groups and substituents, strongly support a dissociative mechanism for these radical nucleophilic displacement reactions.
Preparation of Functionalized Dialkylzinc Reagents via an Iodine-Zinc Exchange Reaction. Highly Enantioselective Synthesis of Functionalized Secondary Alcohols
Rozema, Michael J.,AchyuthaRao, Sidduri,Knochel, Paul
, p. 1956 - 1958 (2007/10/02)
Functionalized dialkylzincs are obtained by the reaction of polyfunctional alkyl iodides with Et2Zn in excellent yield.Their treatment with aldehydes, in the presence of the titanium catalyst 6, affords functionalized secondary alcohols with high enantios
ORGANIC REACTIONS AT ALUMINA SURFACES. AN EXTREMELY SIMPLE, CONVENIENT AND SELECTIVE METHOD FOR ACETYLATING PRIMARY ALCOHOLS IN THE PRESENCE OF SECONDARY ALCOHOLS.
Posner, Gary H.,Oda, Mitsunori
, p. 5003 - 5006 (2007/10/02)
Stirring primary-secondary diols in ethyl acetate solvent over Woelm alumina leads to the corresponding primary monoacetates simply, conveniently, and in good yields.In this way, primary hydroxyalkylphenols are converted into acetoxyalkylphenols, and primary arylamines are transformed into the corresponding acetamides.
