Highly enantioselective direct aldol reactions catalyzed by proline derivatives based on a calix[4]arene scaffold in the presence of water

Synlett

Volumn , Issue 14, 2009, Pages 2356-2360

  Li, Zheng Yi ^a   Chen, Jia Wen ^a   Wang, Leyong ^a   Pan, Yi ^b  

^a NANJING UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

Aldol reaction; Calix 4 arene; Organocatalyst; Proline; Water

Indexed keywords

CALIXARENE; PROLINE DERIVATIVE; WATER;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY;

EID: 69449097485     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217710     Document Type: Article

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43. General procedure for asymmetric aldol reactions: Catalyst 1 (2 mol%) was added to a suspension of aldehyde (1.0 mmol) and ketone (3.0 mmol) in water (324 μL, 18 mmol) at room temperature. The mixture was allowed to stir for the given time, then ethyl acetate (10 mL) and anhydrous MgSO4 (0.6 g) were added. After filtration, the solvent was evaporated under vacuum and the crude products were purified by flash chromatography (hexane-EtOAc). The anti/syn ratio (diastereoselectivity) and enantiomeric excess (enantioselectivity) were determined by chiral HPLC analysis (see ref 24).
44. R(minor) = 43.5 min; 98% ee. For further data on 7 and HPLC spectra, see Supporting Information.
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