86359-03-7Relevant academic research and scientific papers
Nucleophilic acylation of o-quinone methides: An umpolung strategy for the synthesis of α-aryl ketones and benzofurans
Mattson, Anita E.,Scheidt, Karl A.
, p. 4508 - 4509 (2007)
The synthesis of α-aryl ketones is accomplished by the direct nucleophilic acylation of o-quinone methide electrophiles. In this process, two reactive intermediates, carbonyl anions and o-quinone methides, are generated in one flask upon treatment of the corresponding thiazolium carbinols and silyl protected phenols with a soluble fluoride source. These intermediates then undergo productive addition reactions to afford the desired α-aryl ketone adducts. This new strategy has been applied to a short synthesis of the natural product demethylmoracin I. Copyright
REDUCTION PAR LES SELS CHROMEUX DE BROMURES BENZYLIQUES ORTHO-O-ACYLES AVEC TRANSPOSITION DU GROUPEMENT ACYLE DE L'ESTER: ACCES AUX ORTHO-HYDROXYBENZYL CETONES NON MASQUEES ET UNE NOUVELLE PREPARATION DE BENZO(B)FURANNES SUBSTITUES EN POSITION-2
Ledoussal, B.,Gorgues, A.,Coq, A. Le
, p. 5841 - 5852 (2007/10/02)
The ?-bonded organochromium (III) complexes resulting from the reduction of ortho-O-acyl benzylic bromides 1 with CrCl2 undergo an 1,5-transposition of the ester acyl functional group which allows, through selected experimental conditions either a selective access to the unmasked ortho-hydroxybenzyl ketones 2 or a new preparation of the 2-substituted benzofurans 3.The scope and limitations of the method are presented.
