157020-06-9

Upstream product

• 360068-90-2 (S)-(-)-α,α-di(4-vinylphenyl)-2-[(N-ethoxycarbonyl)pyrrolidine]methanol 
• 477961-03-8 2-[hydroxy[bis(4-vinylphenyl)]methyl]pyrrolidine-1-carboxylic acid tert-butyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 18120-63-3 (4-vinylphenyl)magnesium bromide 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 7459-73-6 (4-Vinylphenyl)magnesium chloride 
• 1073-67-2 4-vinylbenzyl chloride 

Downstream Products

• 477961-09-4 1-[2-[hydroxy[bis(4-vinylphenyl)]methyl]pyrrolidin-1-yl]-1-propanone 
• 1262281-20-8 (S)-α,α-bis(4-vinylphenyl)prolinol trimethylsilyl ether 

Relevant academic research and scientific papers

Immobilization of chiral ligands on polymer fibers by electron beam induced grafting and applications in enantioselective catalysis

(Equation presented) Styrenic TADDOL and L-prolinol-derived monomers were immobilized on polyethylene fibers by electron beam induced preirradiation grafting using styrene as comonomer. The polymer-supported chiral ligands were utilized as catalysts in th

POLYMER SUPPORTED FLUORINATED ORGANOCATALYST

Polymer supported fluorinated compound of formula I, wherein the meaning for each R1 is as disclosed in the description. These compounds are useful as catalysts, particularly in Michael addition reactions under continuous flow.

Organocatalytic Enantioselective Continuous-Flow Cyclopropanation

A set of six solid-supported diarylprolinol catalysts (varying on the anchoring strategy and the type of polymeric support) has been prepared and applied to the enantioselective cyclopropanation reaction. The selected candidate allows implementation of a long flow experiment (48 h) and generates a library of 12 cyclopropanes by sequential flow experiments. The mildness and utility of the method have enabled a telescoped process in which the outstream is directly used in a Wittig flow reaction.

Translating the Enantioselective Michael Reaction to a Continuous Flow Paradigm with an Immobilized, Fluorinated Organocatalyst

A novel polymer-supported fluorinated organocatalyst has been prepared and benchmarked in the enantioselective Michael addition of aldehydes to nitroalkenes. The system has proven to be highly efficient and displays excellent selectivities (er and dr) wit

A heterogeneous layered bifunctional catalyst for the integration of aerobic oxidation and asymmetric C-C bond formation

The design and synthesis of a heterogeneous bifunctional chiral catalyst for the sequential aerobic oxidation-asymmetric Michael reactions between primary allylic alcohols and dibenzyl malonate are described. Interestingly, we found that layering bimetallic nanoparticles over the organocatalyst, within the chiral composite material, is crucial for catalytic activity.

Superparamagnetic nanoparticle-Supported (S)-diphenyl- prolinol trimethylsilyl ether as a recyclable catalyst for asymmetric Michael addition in water

A new superparamagnetic nanoparticle-supported (S)-diphenylprolinol trimethylsilyl ether (Jorgensen-Hayashi catalyst) was synthesized and applied for the asymmetric Michael addition of aldehydes to nitroalkenes in water, which gives products in moderate t

Oxazaborolidines as functional monomers: Ketone reduction using polymer-supported Corey, Bakshi, and Shibata catalysts

The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. While the pendant-bound system shows reduced stereoselectivity, the cross-linked version affords enantioselectivities almost identical to those of the solution-phase model.

Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones

Five prolinol-based chiral auxilaries have been compared for the stereoselective synthesis of γ-butyrolactones via the sequence of N-acylation, Cα-allylation, and iodolactonization under both solution-phase and solid-phase conditions. Comparisons of stereoselectivity of both the Cα-allylation and iodolactonization processes indicate that incorporation of a non-C2-symmetric auxiliary as a polymer cross-link gives results superior to those obtained either in solution or with other non-C2-symmetric auxiliaries and comparable to those observed using a polymer-supported pseudo-C2-symmetric auxiliary.