162299-82-3

Upstream product

• 54125-02-9 danishefsky's diene 
• 555-16-8 4-nitrobenzaldehdye 
• 71735-01-8 (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene 
• 194233-66-4 (1E)-3-{[tert-butyl(dimethyl)silyl]oxy}-N,N-dimethyl-1,3-butadien-1-amine 
• 59414-23-2 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene 
• 1197206-96-4 C₁₄H₁₇NO₆ 
• 162181-12-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester 
• 162299-79-8 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester 

Downstream Products

• 255912-53-9 (2S,4S)-2-(4-Nitro-phenyl)-3,4-dihydro-2H-pyran-4-ol 
• 36567-72-3 (S)-3-hydroxy-3-phenylpropanoic acid 
• 255912-54-0 tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane 
• 90564-32-2 (S)-3-hydroxy-3-(4'-nitrophenyl)propanoic acid 

Relevant academic research and scientific papers

Barriers to enantiocontrol in Lewis acid catalyzed hetero-Diels-Alder reactions

Lewis bases, including reactant aldehydes, inhibit the rate of conversion for cycloaddition and those, like aldehydes or nitriles, cause a decrease in enantiocontrol due to the Lewis acidity of the activated complex.

Azotides as Modular Peptide-Based Ligands for Asymmetric Lewis Acid Catalysis

Synthesis of azotides and evaluation of these as ligands for enantioselective Lewis acid catalysis is reported. The ligands were readily prepared from the chiral pool of amino acids and perform well in the cobalt(II)-catalyzed formation of asymmetric hete

Enantiopure (P)- and (M)-3,14-bis(o-hydroxyaryl)tetrahydrobenzo[5]helicenediols and their helicene analogues: Synthesis, amplified circularly polarized luminescence and catalytic activity in asymmetric hetero-Diels–Alder reactions

Three pairs of enantiopure (P)- and (M)-3,14-bis(o-hydroxyaryl)tetrahydrobenzo[5]helicenediols (ArOH-H[5]HOLs), and enantiomers (P)- and (M)-3,14-bis(o-hydroxyphenyl)benzo[5]helicene-diols (PhOH-[5]HOLs) were designed and synthesized. It was found that co

A Cr(salen)-based metal-organic framework as a versatile catalyst for efficient asymmetric transformations

A porous Cr(salen)-MOF can serve as an efficient and effective heterogeneous catalyst for a series of important asymmetric transformations including the Nazarov cyclization, aminolysis reaction, and Diels-Alder and hetero Diels-Alder reactions, resulting

A Family of Chiral Ferrocenyl Diols: Modular Synthesis, Solid-State Characterization, and Application in Asymmetric Organocatalysis

Readily available chiral diol scaffolds are useful as sources of chirality for asymmetric synthesis, however, few such scaffolds are readily available in enantiopure form. Reported herein is a cheap and modular synthesis of a novel family of chiral ferroc

cis-2,5-diaminobicyclo[2.2.2]octane, a new scaffold for asymmetric catalysis via salen-metal complexes

Chemical equations presented. A new C2 symmetric salen scaffold based on cis-2,5-diaminobicyclo[2.2.2]octane has been synthesized that forms complexes with a wide range of metals. The chromium(III) complex is shown to catalyze the hetero-Diels-

Solvent enhancement of reaction selectivity: A unique property of cationic chiral dirhodium carboxamidates

1,3-Dipolar cycloaddition reactions of nitrones with α,β- unsaturated aldehydes catalyzed by a cationic chiral dirhodium(II,III) carboxamidate with (R)-menthyl (S)-2-oxopyrrolidine-5-carboxylate ligands in toluene increase reaction rates, give optimum regioselectivities, and enhance stereoselectivities compared to the same reactions performed in traditionally used halocarbon solvents. Rate and enantioselectivity enhancements were also obtained in hetero-Diels-Alder and carbonyl-ene reactions performed in toluene over those obtained in dichloromethane using the diastereomeric chiral cationic dirhodium(II,III) carboxamidate with (S)-menthyl (S)-2-oxopyrrolidine-5- carboxylate ligands. These enhancements are attributed to diminished or absent association of toluene with the catalyst which lessens the relative importance of the uncatalyzed background reaction, and they may also be a consequence of different coordination angles for aldehyde association with rhodium in the different solvent environments. Overall, the enhancement of reaction rates and selectivities with cationic chiral dirhodium(II,III) carboxamidates in toluene suggests broad applications for them in Lewis acid catalyzed reactions.

Evaluation of catalyst acidity and substrate electronic effects in a hydrogen bond-catalyzed enantioselective reaction

A modular catalyst structure was applied to evaluate the effects of catalyst acidity in a hydrogen bond-catalyzed hetero Diels-Alder reaction. Linear free energy relationships between catalyst acidity and both rate and enantioselectivity were observed, wh

Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates

The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels-Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3- butadiene (Rawal's diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol% of

Asymmetric direct aldol reactions of acetoacetals catalyzed by a simple chiral primary amine

(Chemical Equation Presented) An asymmetric direct aldol reaction of acetoacetals is described. Under the catalysis of a simple chiral primary amine, the direct aldol reactions of acetoacetals occur exclusively on the γ-position to give vinylogous-type al