Download PDF
Synfacts 2010(3): 0353-0353  
DOI: 10.1055/s-0029-1219408
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Phase-Transfer-Catalyzed Alkylations by Ring-Opening of Sulfamidates

Contributor(s): Benjamin List, Lars Ratjen
T. A. Moss, B. Alonso, D. R. Fenwick, D. J. Dixon*
University of Oxford, The University of Manchester and Pfizer Global Research & Development, Sandwich, UK
Further Information

Publication History

Publication Date:
18 February 2010 (online)

    Permissions and Reprints

Significance

The authors report the enantio­selective alkylation of 1,3-dicarbonyl compounds, such as 1, utilizing cyclic N-protected sulfamidates 2. Under phase-transfer-catalyzed conditions using a cinchona alkaloid derived salt and cesium carbonate as base, the desired products were ­obtained in good yields with high stereo­control. Various pro-nucleophiles were applied, among them five- and six-membered rings with different substitution patterns. Likewise the cyclic sulfamidates were not limited to six-membered rings; five-membered electrophiles were tolerated, along with sulfamidates bearing a stereocenter, thus giving rise to diastereoselective versions of the transformation.