Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 347, Issue 9, Pages 1207-1211Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505097
Keywords
benzoin condensation; cyanide catalysis; ketones; phosphate ester; rearrangement; umpolung
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Acyl phosphonates have been utilized as new acyl donors for cyanide-catalyzed benzoin-type reactions. Cyanation of acyl phosphonates, followed by a [1,2]-phosphoryl migration generates the active acyl anion intermediate. The presumed (cyano)phosphate anion reacts with a variety of aryl aldehydes to yield phosphate ester-protected, unsymmetrical benzoins in good to excellent yields. The unsymmetrical benzoin product can be obtained after deprotection of the phosphate ester with an aqueous amine solution.
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