Can a chiral catalyst containing the same ligand/metal components promote the formation of both enantiomers enantioselectively? The bis(oxazoline)-magnesium perchlorate-catalyzed asymmetric Diels-Alder reaction

Desimoni, G.; Faita, Giuseppe; Invernizzi, Anna Gamba; Righetti, P. P.

doi:10.1016/s0040-4020(97)00433-x

Cited by 66 publications

(35 citation statements)

References 56 publications

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“…[108,109] The magnesium(II)-based catalysts exhibited a linear relationship between the ee value of ligand 117 and that of the reaction products (126 or 128). A significant (+)-NLE was observed in both cycloadditions catalyzed by the Zn II complex.…”

Section: Diels-alder Reactionsmentioning

confidence: 99%

Nonlinear Effects in Asymmetric Catalysis

Satyanarayana¹,

Abraham²,

Kagan³

2008

Angew Chem Int Ed

500

273

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There is a need for the preparation of enantiomerically pure compounds for various applications. An efficient approach to achieve this goal is asymmetric catalysis. The chiral catalyst is usually prepared from a chiral auxiliary, which itself is derived from a natural product or by resolution of a racemic precursor. The use of non-enantiopure chiral auxiliaries in asymmetric catalysis seems unattractive to preparative chemists, since the anticipated enantiomeric excess (ee) of the reaction product should be proportional to the ee value of the chiral auxiliary (linearity). In fact, some deviation from linearity may arise. Such nonlinear effects can be rich in mechanistic information and can be synthetically useful (asymmetric amplification). This Review documents the advances made during the last decade in the use of nonlinear effects in the area of organometallic and organic catalysis.

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Section: Diels-alder Reactionsmentioning

confidence: 99%

Nonlinear Effects in Asymmetric Catalysis

Satyanarayana¹,

Abraham²,

Kagan³

2008

Angew Chem Int Ed

500

273

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“…Evans' electron-poor C 2 dissymmetric bis-oxazolines give Cu(I) complexes which are very active and enantioselective in olefin cyclopropanation, [6] while their Mg complexes behave successfully in stereoselective Diels-Alder cycloadditions [7].…”

Section: Introductionmentioning

confidence: 99%

ChemInform Abstract: Free Design of Chiral Diphosphine Chelating Ligands for Stereoselective Homogeneous Catalysis by Assembling Five‐Membered Aromatic Heterocycles.

2002

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“…The catalyst obtained starting from Mg(ClO 4 ) 2 , (+)-1, and 2 equiv of water gives endo-(R)-7a with an endo:exo ratio of 94:6 and an appreciable 89% ee. 8 The use of Mg(OTf) 2 increases the enantioselectivity up to 95% ee. 9 The use of the less reactive dienophile 6b requires higher temperature (−15 • C) to run the cycloaddition with quantitative yields.…”

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confidence: 99%