Enantioselective 1,4-addition of kojic acid derivatives to β-nitroolefins catalyzed by a cinchonine derived sugar thiourea

Reddy, B. V. Subba; Reddy, S. Madhusudana; Swain, Manisha; Dudem, Srikanth; Kalivendi, Shasi V.; Reddy, C. Suresh

doi:10.1039/c3ra47423b

Cited by 19 publications

(15 citation statements)

References 43 publications

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“…In recent studies [6,17] carbohydrate thiourea derivatives showed good enantioselectivities in Michael reactions in acetonitrile and dichloromethane. In addition, according to our unpublished results, cinchona thioureas and squaramides obtain excellent chiral induction in Michael reactions in methyl tert-butyl ether (MTBE).…”

Section: Application Of the New Organocatalysts In Asymmetric Michaelmentioning

confidence: 99%

“…Numerous asymmetric reactions, such as aldol, Mannich, Michael, Henry, amination, Biginelli, cyanosilylation and aza-Morita-BaylisHillman reactions, have been accomplished by these catalysts [3]. Recently, bifunctional thiourea derivatives have been recognized as effective organocatalysts for asymmetric Michael addition reactions [4][5][6]. Therefore, the development of simple and efficient bifunctional thiourea catalysts has great interest.…”

Section: Introductionmentioning

confidence: 99%

“…The interaction between the catalyst and the reactants can be promoted by the protonated nitrogen of the chiral cinchona skeleton (Figure 1) [6]. Michael addition of 2 enolate to β-nitrostyrene (3) [6].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, cinchona derived thiourea catalysts have received special attention in the field of organocatalysis [4,[8][9][10]. The interaction between the catalyst and the reactants can be promoted by the protonated nitrogen of the chiral cinchona skeleton (Figure 1) [6]. Michael addition of 2 enolate to β-nitrostyrene (3) [6].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Three New Bifunctional Glucose-Thiourea Organocatalysts and Their Application in Asymmetric <i>Michael</i> Addition

Nagy¹,

Kozma²,

Kisszékelyi³

et al. 2017

Studia UBB Chemia

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ABSTRACT. Three new glucose-based asymmetric bifunctional organocatalysts containing a 6-aminopyridyl or a 6-methylpyridyl or a cinchona unit were synthesized. Asymmetric Michael addition of pentane-2,4-dione to β-nitrostyrene was catalyzed successfully by these catalysts. In case of the cinchona based glucose-thiourea derivate the S enantiomer of the corresponding Michael adduct was formed with moderate enantiomeric excess in three different solvents.

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Section: Application Of the New Organocatalysts In Asymmetric Michaelmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Three New Bifunctional Glucose-Thiourea Organocatalysts and Their Application in Asymmetric <i>Michael</i> Addition

Nagy¹,

Kozma²,

Kisszékelyi³

et al. 2017

Studia UBB Chemia

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“…at − 10 • C for 4 days to obtain products 89 in 58%-99% yields and good enantioselectivities (Scheme 34). Moreover, Subba Reddy et al 89 reported a similar approach using cinchonine-derived sugar thioureas in 2014, in which the corresponding Michael adducts exhibited promising cytotoxicity against various cancer cell lines.…”

mentioning

confidence: 99%

Kojic acid in organic synthesis

Zirak¹,

Eftekhari‐Sis²

2015

Turk J Chem

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The reactions of kojic acid in organic synthesis are reviewed. The aim of this review is to cover the literature up to the end of 2014, showing the distribution of publications involving kojic acid chemistry in the synthesis of various pyrone containing compounds, pyridine and pyridone heterocycles, and also other organic compounds. First, introductory text about the preparation, biological, and industrial applications, and the chemical properties of kojic acid is given.Then its uses in organic synthesis are presented considering the reaction type.

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The Catalytic, Enantioselective Michael Reaction

et al. 2016

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The catalytic enantioselective Michael reaction is the conjugate addition of a resonance‐stabilized carbanion to an electron‐poor olefin (an αβ‐unsaturated carbonyl compound or a related derivative) mediated by substoichiometric amounts of a chiral catalyst that enables stereocontrol in the newly generated stereocenter(s). This reaction allows the direct enantioselective construction of substituted 1,5‐dicarbonyl compounds or related architectures through the appropriate selection of the enolizable carbonyl compound employed as pronucleophile and the Michael acceptor. A variety of catalyst architectures have been described that make it possible to carry out this reaction with superior levels of chemical efficiency and high enantio‐ and stereocontrol, and also under conditions that tolerate a wide variety of functional groups. Both transition metal catalysis and organocatalysis have been employed as methodological approaches for carrying out this reaction in an enantioselective manner. This chapter describes different catalytic systems and methods developed for achieving enantioselective Michael reactions through the end of 2012, including a detailed mechanistic explanation of the different generic modes of substrate activation operating with each type of catalyst and their associated stereochemical aspects. The intention is to provide researchers interested in applying this methodology to their own synthetic strategies with a suitable starting point for identifying an efficient synthetic approach. In addition, the preparation of selected catalysts that are excellent for a particular pairing of substrates in this reaction, together with practical experimental protocols are described and some examples in which these methodologies have been applied to total synthesis have been included. This chapter is limited exclusively to those examples in which the final Michael addition product is obtained after protonation of the conjugate addition intermediate and therefore, tandem, domino, or cascade processes initiated by Michael reactions lie outside the scope of this work. Supplemental references are provided for articles published after the 2012 cut‐off date through the first half of 2015.

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Enantioselective 1,4-addition of kojic acid derivatives to β-nitroolefins catalyzed by a cinchonine derived sugar thiourea

Cited by 19 publications

References 43 publications

Synthesis of Three New Bifunctional Glucose-Thiourea Organocatalysts and Their Application in Asymmetric <i>Michael</i> Addition

Synthesis of Three New Bifunctional Glucose-Thiourea Organocatalysts and Their Application in Asymmetric <i>Michael</i> Addition

Kojic acid in organic synthesis

The Catalytic, Enantioselective Michael Reaction

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