期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 347, 期 9, 页码 1207-1211出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505097
关键词
benzoin condensation; cyanide catalysis; ketones; phosphate ester; rearrangement; umpolung
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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