910541-17-2

Upstream product

• 10277-74-4 (R)-1-Aminoindane 
• 541-41-3 chloroformic acid ethyl ester 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 

Relevant academic research and scientific papers

Water versus solvent-free conditions for the enantioselective inter- and intramolecular aldol reaction employing l-prolinamides and l-prolinethioamides as organocatalysts

Organocatalysts 1, derived from L-proline and (1S,2R)-cis-l-aminoindan-2-ol or (R)-l-aminoin-dane, are evaluated as promoters in the direct asymmetric aldol reaction between ketones and aromatic aldehydes in the presence of water and under solvent-free reaction conditions. L-Prolinethioamides 1c and 1d exhibited higher enantioselectivity than the corresponding prolinamides 1a and 1b in the model aldol reaction between cyclohexanone and 4-nitro-benzaldehyde in the presence of 4-nitrobenzoic acid as cocatalyst. In particular, L-prolinethioamide 1d (5 mol%), derived from L-proline and (R)-1-amino-indane, is shown as the most efficient organocatalyst studied promoting the direct aldol reaction of cyclo-alkyl, alkyl, and a-functionalized ketones with aromatic aldehydes in the presence of water and under solvent-free reaction conditions employing only 2 equivalents of nucleophile. Generally, anft-aldol products are obtained in high yields and excellent diastereo- and enantioselectivities (up to > 98/2 until syn, up to 98% ee). Solvent-free conditions give slightly higher dr and ee than using water as solvent. In addition, organocatalyst Id can be easily recovered by extractive work-up and reused. Prolinethio-amide Id (5 mol%) in combination with 4-NO2C6H4CO2H (5 mol%) is also a very effective or-ganocatalytic system for the asymmetric solvent-free intramolecular Haj os-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity (up to 88% ee) to other reported catalysts in organic solvents.

Evaluation of ligands for ketone reduction by asymmetric hydride transfer in water by multi-substrate screening

Various ligands for the ruthenium-catalyzed enantioselective reduction of ketones in water have been investigated. Multi-substrate reactions have been carried out for the comparison of various proline amides and aminoalcohol ligands. Two sets of six aromatic ketones have been selected in order to evaluate the enantiomeric excesses of all the resulting alcohols by a single chromatographic analysis. The proline amide derivative prepared from (1R,2S)-cis-aminoindanol revealed as the best ligand for most of the ketones used in the multi-substrate reductions. This ligand has been employed for the enantioselective reduction of a variety of other aromatic ketones and in all cases the enantiomeric excesses were improved compared to those obtained with phenylprolineamide used in our previous work.

Prolinamides versus prolinethioamides as recyclable catalysts in the enantioselective solvent-free inter- and intramolecular aldol reactions

A solvent-free asymmetric and direct anti-aldol reaction of aliphatic ketones with aromatic aldehydes catalyzed by recyclable L-prolineamides and L-prolinethioamides 3 is studied. The L-prolinethioamide 3d (5 mol%), derived from L-Pro and (R)-1-aminoindane, is the most efficient catalyst for this process affording the anti-aldol adducts in high yields with excellent diastereo-and enantioselectivities (up to >98/2 dr, up to 98% ee) at 0°C or room temperature. Prolinethioamide 3d is an effective organocatalyst for the first asymmetric, solvent-free, intramolecular Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity (up to 88% ee) to reported catalysts in organic solvents. Moreover, organocatalyst 3d can be easily recovered and reused by a simple acid/base extraction.

Asymmetric conjugate addition of ketones to β-nitrostyrenes by means of 1,2-amino-alcohol-derived prolinamides as bifunctional catalysts

Different L-prolinamides 21, prepared from L-proline and chiral β-amino alcohols are active bifunctional catalysts for the direct nitro-Michael addition of ketones to β-nitrostyrenes. In particular, catalyst 21e, prepared from L-proline and (1S,2R?)-cis-1

Enantioselective conjugate addition of ketones to β-nitrostyrenes catalyzed by 1,2-amino alcohol-derived prolinamides

Various l-prolinamides 14, prepared from l-proline and chiral β-amino alcohols, are active bifunctional catalysts for the direct nitro-Michael addition of ketones to β-nitrostyrenes. In particular, catalyst 14e prepared from l-proline and (1S,2R)-cis-1-am