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Volumn , Issue 19, 2008, Pages 3031-3035

N-Tosyl-(Sa)-binam-L-prolinamide as highly efficient bifunctional organocatalyst for the general enantioselective solvent-free aldol reaction

(3) Guillena, Gabriela a Nájera, Carmen a Viózquez, Santiago F a

a UNIVERSITY OF ALICANTE (Spain)

Author keywords

Aldol reactions; Enantio selective; Ketone; Organocatalyzed; Solvent free

Indexed keywords

4 NITROBENZALDEHYDE; ALDEHYDE; AMIDE; BENZOIC ACID; CYCLOHEXANONE; KETONE; N TOSYL BINAM LEVO PROLINAMIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 57649120787 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1087349 Document Type: Article

Times cited : (57)

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- Representative Experimental Procedure: Anhydrous Solvent-Free Conditions: To a mixture of the corresponding aldehyde (0.25 mmol, catalyst 2 (0.0125 mmol, 6.5 mg) and benzoic acid (0.0025 mmol, 0.3 mg) at 0°C was added the corresponding ketone (0.5 mmol, The reaction was stirred until the aldehyde was consumed (monitored by TLC, Then, the crude product was diluted in CH2Cl2 (10 mL, silica gel was added and the solvent was evaporated in vacuo. The resulting residue was purified by flash chromatography (hexanes-EtOAc) to yield the pure aldol product. Wet Solvent-Free Conditions: To a mixture of the corresponding aldehyde (0.25 mmol, catalyst 2 (0.0125 mmol, 6.5 mg, benzoic acid (0.0025 mmol, 0.3 mg, H2O (33 μL) was added at 0°C followed by the corresponding ketone (0.5 mmol, The reaction was stirred until the aldehyde was consumed. The crude product was diluted in CH2Cl2 10 mL, MgSO
- 4 was added and filtered. To the filtrate, silica gel was added and the above purification procedure was followed to obtain the aldol product.

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