727683-89-8

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 1215006-72-6 (R)-3,6-dihydro-3,3-dimethyl-2-(4-nitrophenyl)-2H-pyran 
• 1215006-78-2 (1S,3S,6R)-2,2-dimethyl-3-(4-nitrophenyl)-4,7-dioxabicyclo[4.1.0]heptane 
• 1360110-23-1 (S)-2,2-dimethyl-1-(4-nitrophenyl)-3-oxopropyl (diethoxyphosphoryl)acetate 

Relevant academic research and scientific papers

Direct, pyrrolidine sulfonamide promoted enantioselective aldol reactions of α,α-dialkyl aldehydes: Synthesis of quaternary carbon-containing β-hydroxy carbonyl compounds

A procedure has been developed for direct, asymmetric aldol reactions of α,α-dialkyl aldehydes with aromatic aldehydes, which produces quaternary carbon-containing β-hydroxy carbonyl compounds. The processes, promoted by the organocatalyst (S) pyrrolidine sulfonamide, take place in high yields with exceptionally high levels of enantioselectivities.

Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules

We report the synthesis and evaluation of prolinamide organocatalysts that incorporate aminouracils. The features of these catalysts are enhanced NH acidity of the amide because of the electron-withdrawing nature of the heterocycle, an additional hydrogen-bond donor at the α or β positions of this functional group (using 6-aminouracil or 5,6-diaminouracil respectively), and it can be recovered due to its low solubility and used again without decreasing the enantioselectivity. A unique feature of these systems is the self-assembly capability with complementary modules by Watson–Crick interactions. These supramolecular adducts behave differently from the catalyst alone, some of them have lower performance but others improve the selectivity of the product. Therefore, this approach avoids the synthesis of many catalysts.

L-isoleucine in a choline chloride/ethylene glycol deep eutectic solvent: A reusable reaction kit for the asymmetric cross-aldol carboligation

l-Isoleucine is able to catalyze the cross-aldol reaction between cyclohexanone and aromatic aldehydes in a deep eutectic solvent consisting in choline chloride and ethylene glycol, rendering products with high diatereo- and enantioselectivity. This proto

Role of additives in chiral amine-catalyzed direct aldol reaction

A systematic study of chiral adducts derived from amines as catalysts for aldol reaction revealed that enantioselective outcome depends on the chiral enamine intermediate and not the face-selective activation of aldehyde. A simple addition compound of proline and 8-hydroxy quinoline was found to be a good catalyst. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Isoleucine-catalyzed direct asymmetric aldol addition of enolizable aldehydes

Isoleucine-catalyzed direct enantioselective aldol additions between enolizable aldehydes are reported. Intermediate acetal structures dictate the configurative outcome and were supported by a hydrogen bond. This direct isoleucine-catalyzed aldol addition represents a welcome complement to both proline- and histidine-catalyzed aldol additions of enolizable aldehydes.

Enantio- and diastereoselective synthesis of β,γ,γδ, -tetrasubstituted -methylene -δ-lactones

The synthesis of two -(diethoxyphosphoryl)-,-unsaturated -lactones with 98% ee has been developed using (S)-3-aryl-3-hydroxy-2,2-dimethylpropanals, easily accessible via direct, asymmetric organocatalytic aldol reaction, as the starting materials. The lac

Chiral zwitterions from vicinal diamines: Effective and recoverable asymmetric enamine catalysts

A series of chiral zwitterionic vicinal diamines were designed and synthesized. The zwitterionic catalysts demonstrated good reactivity and enantioselectivity in asymmetric enamine-based transformations and could be readily recycled and reused for four ti

Chiral primary-tertiary diamine-bronsted acid salt catalyzed syn-selective cross-aldol reaction of aldehydes

(Figure presented) Highly syn-selective cross-aldol reaction of aldehydes has remained a challenging subject in the field of aminocatalysis. To achieve this end, chiral primary amines have been explored and the primary-tertiary diamine-Bronsted acid salts are found to promote the cross-aldol reactions of aldehydes with high activity and syn selectivity. Among various vicinal diamines screened, l-phenylalanine derived 2a/TfOH conjugate is identified as the optimal catalyst, showing good catalytic activity (up to 97% yield) and high syn selectivities (syn/anti up to 24:1, 87% ee). The current catalysis works selectively with small aliphatic aldehydes donors such as propionaldehyde and isobutyraldehyde, but not with aliphatic aldehydes bearing larger β-substitute (>Me). In addition, the use of 2a/TfOH conjugate has also enabled the first syn-selective cross-aldol reactions of glycoaldehyde donors.

Chiral amine-polyoxometalate hybrids as recoverable asymmetric enamine catalysts under neat and aqueous conditions

Solid acid-chiral amine hybrids have been synthesized and explored as recyclable and reusable enamine-type asymmetric catalysts. Simple chiral amine-polyoxometalate (CA-POM) hybrids were identified as the optimal catalysts to promote a range of enamine-ba

Hydroxy-α-amino acids modified by ionic liquid moieties: recoverable organocatalysts for asymmetric aldol reactions in the presence of water

New chiral ionic liquids bearing proline, serine or threonine moieties were synthesized. Compounds that contain 1-dodecylimidazolium or 4-(5-n-nonyl)-pyridinium cations and NTf2 or PF6 anions efficiently catalyze the asymmetric aldol reaction between aldehydes and ketones in the presence of water to generate aldols with high distereo- (up to 98:2) and enantioselectivity (up to >99% ee). 4-Hydroxyproline modified by the 4-(5-n-nonyl)-pyridinium hexafluorophosphate moiety retains its activity and selectivity over at least eight reaction cycles.