Journal ArticleDOI
A study of substituent effects on the enantioselective trimethylsilylcyanation of benzaldehyde catalyzed by chiral Schiff base–titanium(IV) complexes
Angeles Gama,Lucía Z. Flores-López,Gerardo Aguirre,Miguel Parra-Hake,Ratnasamy Somanathan,Thomas E. Cole +5 more
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In this article, chiral Schiff base ligands derived from tert-butyl salicylaldehydes bearing electron withdrawing and donating groups were synthesized by reaction with various substituted chiral amino alcohols.Abstract:
New chiral Schiff base ligands derived from tert -butyl salicylaldehydes bearing electron withdrawing and donating groups were synthesized by reaction with various substituted chiral amino alcohols. These ligands were used with titanium tetraisopropoxide to study steric and electronic effects on the enantioselectivity of the trimethylsilylcyanation of benzaldehyde. ZINDO calculations are in agreement with the experimental results on the intermediate complexes, which indicate that the steric effects of the substituents are more important than the electronic ones.read more
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Lewis acid catalyzed asymmetric cyanohydrin synthesis.
TL;DR: This paper presents a meta-analyses of C1-Symmetric Schiff Bases for the Asymmetric Cyanation of Ketones using Boron-Based Catalytic Systems and concludes that these systems are likely to be incompatible with each other.
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Multidentate unsymmetrically-substituted Schiff bases and their metal complexes: Synthesis, functional materials properties, and applications to catalysis
Xiang Liu,Xiang Liu,Carolina Manzur,Néstor Novoa,Salvador Celedón,David Carrillo,Jean-René Hamon +6 more
TL;DR: A review of the recent developments of unsymmetrically-substituted multidentate Schiff bases whose steric and electronic characteristics are easily manipulated by selecting suitable condensing aldehydes or ketones and primary amines, and on their metal complexes can be found in this article.
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In the arena of enantioselective synthesis, titanium complexes wear the laurel wreath.
Diego J. Ramón,Miguel Yus +1 more
TL;DR: The aim of this work was to provide a chronology of key events and events leading to and following thioether Oxidation, as well as to investigate its role in the development of enantioselective techniques.
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Metal catalyzed asymmetric cyanation reactions
TL;DR: In this article, the authors discuss the various methods for catalytic asymmetric synthesis of cyanohydrins derived from both aldehydes and ketones using different sources of cyanide.
Journal ArticleDOI
Recent Progress in the Chemically Catalyzed Enantioselective Synthesis of Cyanohydrins
TL;DR: The catalytic enantioselective cyanation of aldehydes and ketones has received growing attention because the resulting enantiomerically pure cyanohydrins are versatile building blocks for many biologically active compounds as mentioned in this paper.
References
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Comprehensive organic functional group transformations II
TL;DR: In this article, the synthesis of carbon with no attached heteroatoms was studied, as well as carbon with two attached heteroams with at least one carbon-to-heteroatom multiple link.
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A Practical Method for the Large-Scale Preparation of [N,N'-Bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]manganese(III) chloride, a Highly Enantioselective Epoxidation Catalyst
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Cyanohydrins in Nature and the Laboratory: Biology, Preparations, and Synthetic Applications.
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The Mechanistic Basis for Electronic Effects on Enantioselectivity in the (salen)Mn(III)-Catalyzed Epoxidation Reaction
Michael Palucki,Nathaniel S. Finney,Paul J. Pospisil,Mehmet L. Guler,Toyohisa Ishida,Eric N. Jacobsen +5 more
TL;DR: In this article, it was shown that enantioselectivity in the (salen)mn-catalyzed asymmetric epoxidation reaction correlates directly with the electronic properties of the ligand substituents.
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Catalytic Asymmetric Oxidation of tert-Butyl Disulfide. Synthesis of tert-Butanesulfinamides, tert-Butyl Sulfoxides, and tert-Butanesulfinimines
TL;DR: The first example of the catalytic asymmetric oxidation of tert-butyl disulfide is described and thiosulfinate ester 2 is obtained with 91% enantiomeric excess in yields of ≥92% on scales as large as 1 mol.