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Relevant academic research and scientific papers

Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes

The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical yields (up to 86 %) with excellent diastereoselectivities (endo/exo, up to 96:4) and enantioselectivities (up to 97 % ee). Furthermore, the obtained isoxazolidines were easily converted into γ-amino diols that contain three contiguous stereogenic centers.

Enantioselective 1,3-dipolar cycloadditions of nitrones with unsaturated aldehydes promoted by a recyclable tetraarylphosphonium supported imidazolidinone catalyst

The tetraarylphosphonium supported chiral imidazolidinone catalyzes the enantioselective 1,3-dipolar cycloadditions of nitrones and α,β- unsaturated aldehydes to provide isoxazolidine aldehydes in good yields with excellent diastereo- and enantioselectivi

A magnetoclick imidazolidinone nanocatalyst for asymmetric 1,3-dipolar cycloadditions

A 1,3-dipolar azide-alkyne cycloaddition has been used to prepare a magnetic nanoparticle immobilized MacMillan catalyst that catalyzes the enantioselective 1,3-dipolar cycloaddition between nitrones and α,β-unsaturated aldehydes. The catalyst can be recovered and recycled for five consecutive runs without any significant loss in yields and diastereo- and enantioselectivities of the isoxazolidines. Copyright

Synthesis and application of a recyclable ionic liquid-supported imidazolidinone catalyst in enantioselective 1,3-dipolar cycloaddition

The synthesis of recyclable ionic liquid-supported imidazolidinone catalyst I and its application in 1,3-dipolar cycloaddition of nitrone with α,β-unsaturated aldehyde with high performance were described. Most importantly, the catalyst I can be recovered

A new organocatalyst for 1,3-dipolar cycloadditions of nitrones to α,β-unsaturated aldehydes

The triflate salt resulting from the treatment of diphenyl-S-prolinol with trimethylsilyl triflate, catalyzes the addition of nitrones to α,β-unsaturated aldehydes to provide isoxazolidines in high yields and excellent diastereo- and enantioselectivities.

Lewis acid catalyzed asymmetric cycloadditions of nitrones: α′-hydroxy enones as efficient reaction partners

(Chemical Equation Presented) A fine pair: Excellent levels of regio-, endo/ exo-, diastereo-, and/or enantioselectivity are attained in the Cu-catalyzed cycloaddition of nitrones with α′-hydroxy enones (see scheme). The resulting adducts can be further e

Enantioselective 1,3-Dipolar Cycloadditions of Unsaturated Aldehydes Promoted by A Poly(ethylene glycol)-Supported Organic Catalyst

We have developed a polymer-supported version of MacMillan's catalyst by anchoring a tyrosine-derived imidazolidin-4-one by means of a spacer to the monomethyl ether of poly(ethylene glycol) (MW = 5000 Da). The supported organic catalyst was employed in some 1,3-dipolar cycloadditions involving α,β-unsaturated aldehydes and nitrones. The products were obtained in enantiomeric excesses very similar to those observed with the non-supported catalyst, but the chemical yields were somewhat lower. Exploiting the solubility profile of the polymeric support, the catalyst was readily separated from the reaction products, recovered, and recycled. Catalyst recycling was accompanied by a very marginal erosion (if any) of the enantioselectivity and a more-substantial decrease in chemical efficiency. We ascribe the latter phenomenon mainly to the intrinsic instability of the catalyst under the reaction conditions, which is, however, a common feature of both the non-supported and supported catalysts. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.