309918-44-3

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 3376-26-9 N-Benzylidenbenzylamin-N-oxid 
• 3376-26-9 N-Benzylidenebenzylamine N-oxide 
• 77681-22-2 (Z)-N-benzylidenebenzylamine N-oxide 
• 123-73-9 crotonaldehyde 
• 932-90-1 Benzaldoxime 
• 622-30-0 N-benzyl hydroxylalmine 
• 100-52-7 benzaldehyde 

Downstream Products

• 309918-73-8 ((3R,4R,5R)-2-benzyl-5-methyl-3-phenylisoxazolidin-4-yl)methanol 
• 309918-86-3 (1R,2R,3R)-1-(benzylamino)-2-(hydroxymethyl)-1-phenyl-butan-3-ol 

Relevant academic research and scientific papers

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.

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.

Hydrazide-catalyzed 1,3-dipolar nitrone cycloadditions

The triflate salts of cyclic hydrazides function as asymmetric catalysts for the [3+2]cycloadditions of nitrones with α,β-unsaturated aldehydes. The camphor-derived hydrazides show a preference for the exo isomers during these reactions, providing a compliment to other organically catalyzed dipolar cycloadditions. Enantiomeric excesses as high as 93% were realized for the exo isomers, while some endo products were obtained in 94% ee.

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.

Assessment of non-standard reaction conditions for asymmetric 1,3-dipolar organocatalytic cycloaddition of nitrone with α,β-unsaturated aldehydes

Non-standard experimental conditions can often enhance organocatalytic reactions considerably. The current study explores the effectiveness of a range of non-standard reaction conditions for the asymmetric organocatalytic 1,3-dipolar cycloaddition of a nitrone with α,β-unsaturated aldehydes. The influence of ionic liquids, high-pressure conditions, ultrasound, microwave irradiation and ballmilling was tested as well as the flow process. Because of the low reactivity of the nitrone and unsaturated aldehydes in the 1,3-dipolar cycloaddition, cycloadducts were isolated in only moderate yields from the majority of experiments. However, high diastereo- and enantioselectivities were observed in ionic liquids under solvent-free conditions and in the flow reactor.

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

The highly enantioselective 1,3-dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde catalyzed by hybrid diamines

1,3-Dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde can be catalyzed by hybrid diamines, obtained from (S)-BINAM and l-α-amino acids. The hybrid of (S)-BINAM and l-Phe was found to be the best organocatalyst. Products were o

Hybrid diamines derived from 1,1′-binaphthyl-2,2′-diamine and α-amino acids as organocatalysts for 1,3-dipolar cycloaddition of aromatic nitrones to (E)-crotonaldehyde

Homochiral derivatives of 1,1′-binaphthyl-2,2′-diamine and various α-amino acids were prepared using a convenient procedure. They were tested as organocatalysts for 1,3-dipolar cycloaddition of aromatic nitrones to (E)-crotonaldehyde. The L-phenylalanine-