Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 41, Pages 13089-13093Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404215
Keywords
acetaldehyde; cross-aldol; recycling; site-isolation; wolf and lamb
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Funding
- Institute of Chemical Research of Catalonia (ICIQ) Foundation
- MINECO [CTQ2012-38594-C02-01, SEV-2013-0319]
- DEC Generalitat de Catalunya [2014SGR827]
- CSC (Chinese Scholarship Council)
- AGAUR (Generalitat de Catalunya)
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Polystyrene-supported (PS) diarylprolinol catalysts 1a (Ar=phenyl) and 1b (Ar=3,5-bis(trifluoromethyl)phenyl) have been developed. Operating under site-isolation conditions, PS-1a/1b 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.
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