Enantioselective synthesis of polycyclic ketones by desymmetrisation of bis(phenylsulfonyl)alkenes with chiral alcoholates. Control of the absolute configuration by a simple modification of the chiral auxiliary

Treatment of polycyclic bis(phenylsulfonyl)alkenes with chiral alcoholates, followed by acidic work-up, affords enantioselectively α-phenylsulfonyl ketones. The enantioselectivity is total with monomethylated hydrobenzoin and of opposite configuration with respect to that obtained with hydrobenzoin...

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Bibliographic Details
Published in:Tetrahedron letters 1999-12, Vol.40 (49), p.8705-8709
Main Authors: Cossu, Sergio, De Lucchi, Ottorino, Peluso, Paola, Volpicelli, Raffaella
Format: Article
Language:English
Subjects:
asymmetric synthesis
desymmetrisation
polycyclic ketones
sulfones
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Summary:Treatment of polycyclic bis(phenylsulfonyl)alkenes with chiral alcoholates, followed by acidic work-up, affords enantioselectively α-phenylsulfonyl ketones. The enantioselectivity is total with monomethylated hydrobenzoin and of opposite configuration with respect to that obtained with hydrobenzoin itself. Thus, starting from a bis(phenylsulfonyl)alkene, it is possible to obtain either the R or S polycyclic ketone by the use of the same chiral auxiliary (hydrobenzoin) and a simple modification (methylation of one of the hydroxy functions). Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01848-1