Journal
TETRAHEDRON
Volume 67, Issue 24, Pages 4378-4384Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.02.023
Keywords
Sulfoxide; Tridentate ligand; Asymmetric oxidation; 1,4-Addition; Hydroacylation
Categories
Funding
- University of Toronto
- Canadian Foundation for Innovation
- Ontario Ministry of Research and Innovation
- Boehringer Ingelheim Ltd. Canada
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Alfred P. Sloan Fellowship
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A series of tris- and bis-sulfoxides were synthesized by multiple asymmetric oxidation of the corresponding sulfides. High enantioselectivities were obtained based on Horeau-type amplification of selectivity. Naphthyl-substituted sulfoxides allowed for higher selectivity and greater ease of purification. These sulfoxides were tested as ligands in rhodium-catalyzed olefin hydroacylation and 1,4-addition of phenyl boronic acid to 2-cyclohexen-1-one. While no enantioinduction was observed in hydroacylation, up to 80% ee was obtained for a tris-sulfoxide and a bis-sulfoxide ligand in the 1,4-addition. Bis-sulfoxides with flexible backbones gave lower and inversed enantioselectivity, suggesting backbone rigidity plays a key role in enantioinduction. (C) 2011 Elsevier Ltd. All rights reserved.
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