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- W2113705552 abstract "Polystyrene-supported (PS) diarylprolinol catalysts 1 a (Ar = phenyl) and 1 b (Ar = 3,5-bis(trifluoromethyl)phenyl) have been developed. Operating under site-isolation conditions, PS-1 a/1 b worked compatibly with PS-bound sulfonic acid catalyst 2 to promote deoligomerization of paraldehyde and subsequent cross-aldol reactions of the resulting acetaldehyde in one pot, affording aldol products in high yields with excellent enantioselectivities. The effect of water on the performance of the catalytic system has been studied and its optimal amount (0.5 equiv) has been determined. The dual catalytic system (1/2) allows repeated recycling and reuse (10 cycles). The potential of this methodology is demonstrated by a two-step synthesis of a phenoperidine analogue (68% overall yield; 98% ee) and by the preparation of highly enantioenriched 1,3-diols 4 and 3-methylamino-1-arylpropanols 5, key intermediates in the synthesis of a variety of druglike structures." @default.
- W2113705552 created "2016-06-24" @default.
- W2113705552 creator A5001877100 @default.
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- W2113705552 creator A5014156830 @default.
- W2113705552 creator A5024128036 @default.
- W2113705552 creator A5058475033 @default.
- W2113705552 date "2014-08-28" @default.
- W2113705552 modified "2023-10-07" @default.
- W2113705552 title "Highly Enantioselective Cross-Aldol Reactions of Acetaldehyde Mediated by a Dual Catalytic System Operating under Site Isolation" @default.
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- W2113705552 doi "https://doi.org/10.1002/chem.201404215" @default.
- W2113705552 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25168085" @default.
- W2113705552 hasPublicationYear "2014" @default.
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