Chiral ionic liquid-catalyzed Biginelli reaction: stereoselective synthesis of polyfunctionalized perhydropyrimidines

Yadav, Lal Dhar S.; Rai, Ankita; Vijai, K.; Awasthi, Chhama

doi:10.1016/j.tet.2007.11.044

Cited by 74 publications

(18 citation statements)

References 45 publications

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“…20). 107 The chiral ILs investigated were amino acid-derived and include L-prolinium sulfate, L-alaninium hexafluorophosphate, and L-threoninium nitrate. The former performed the best among the three.…”

Section: Applications Of Chiral Ionic Liquids Cils In Asymmetric Syntmentioning

confidence: 99%

Chiral ionic liquids: A compendium of syntheses and applications (2005–2012)

Payagala¹,

Armstrong²

2011

Chirality

125

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In recent years, the field of chiral ionic liquids (CILs) has undergone exponential growth. As the technology has advanced, new ways of synthesizing stable and structurally diverse ionic liquids have been established. This has led to heretofore unknown applications of CILs as well as in improving efficiency of previously identified applications. In this review article we have compiled a comprehensive database containing structures and physical properties of notable CILs that have been synthesized during the last 6 years. Their applications in the fields of asymmetric organic synthesis, spectroscopy, and chromatography are also illustrated. This is an expansion of our previous review, which covered the literature before 2005.

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Section: Applications Of Chiral Ionic Liquids Cils In Asymmetric Syntmentioning

confidence: 99%

Chiral ionic liquids: A compendium of syntheses and applications (2005–2012)

Payagala¹,

Armstrong²

2011

Chirality

125

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“…[53] The three-component domino reaction of urea or thiourea derivatives, active methylene components and aromatic aldehydes took place in the presence of catalytic amounts of the CIL (S)-prolinium sulfate (20 mol-%) 44 and THF as solvent. The proline-derived CIL proved to be most suitable, and considerably lower yields, diastereoand enantioselectivities were obtained with the corresponding alanine or threonine-derived CILs.…”

Section: Biginelli Reactionmentioning

confidence: 99%

Applications of Chiral Ionic Liquids

2008

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Despite the rapid growth in chiral ionic liquid (CIL) research, successful applications remained hidden for some time, but are increasing fast nowadays. The major part of this review deals with the use of CILs as solvents, catalysts or ligands in asymmetric synthesis. Chiral recognition abilities in spectroscopic techniques such as NMR, NIR or fluorescence spectroscopy are discussed as well as the application of CILs for separation in chromatography. In this review, we focus entirely on the applications of CILs; publications dealing with design and synthesis of CILs only are not mentioned. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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“…Recently, several synthetic procedures for preparing of DHPMs have been reported, such as the use of a number of Lewis acid catalysts as well as protic acids including Y(NO 3 ) 3 .6H 2 O [8], Cu(BF 4 ) 2 [9], KAl(SO 4 ) 2 .12H 2 O [10], Mg(ClO 4 ) 2 [11], triphenylphosphine [12], Ca(NO 3 ) 2 [13], and H 3 BO 3 [14]. In addition, microwave irradiation [15], ultrasound irradiation [16], and ionic liquid [17] have also been utilized to improve and modify this reaction. As part of our current studies on the development of new catalysts [18,19], herein, we report an efficient and environmentally friendly method for the synthesis of 4-aryl-3,4-dihydropyrimidin-2(1H)-thiones catalyzed by Ni on SiO 2 at room temperature (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%