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

Authors
Cossu, S De Lucchi, O Peluso, P Volpicelli, R
Citation
S. Cossu et al., 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, TETRAHEDR L, 40(49), 1999, pp. 8705-8709
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
49
Year of publication
1999
Pages
8705 - 8709
Database
ISI
SICI code
0040-4039(199912)40:49<8705:ESOPKB>2.0.ZU;2-#
Abstract
Treatment of polycyclic bis(phenylsulfonyl)alkenes with chiral alcoholates, followed by acidic work-up, affords enantioselectively cx-phenylsulfonyl k etones. The enantioselectivity is total with monomethylated hydrobenzoin an d 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 a uxiliary (hydrobenzoin) and a simple modification (methylation of one of th e hydroxy functions). (C) 1999 Elsevier Science Ltd. All rights reserved.