Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of gamma-Thioesters
Author(s)Sun, Jianwei; Fu, Gregory C.
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A method for catalytic asymmetric γ sulfenylation of carbonyl compounds has been developed. In the presence of an appropriate catalyst, thiols not only add to the γ position of allenoates, overcoming their propensity to add to the β position in the absence of a catalyst, but do so with very good enantioselectivity. Sulfur nucleophiles are now added to the three families of nucleophiles (carbon, nitrogen, and oxygen) that had earlier been shown to participate in catalyzed γ additions. The phosphine catalyst of choice, TangPhos, had previously only been employed as a chiral ligand for transition metals, not as an efficient enantioselective nucleophilic catalyst.
Supporting Information Available: Experimental procedures and compound characterization data. This material is available free of charge via the Internet at http://pubs.acs.org.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Journal of the American Chemical Society
American Chemical Society
Sun, Jianwei, and Gregory C. Fu. “Phosphine-Catalyzed Formation of Carbon−Sulfur Bonds: Catalytic Asymmetric Synthesis of γ-Thioesters.” Journal of the American Chemical Society 132 (2010): 4568-4569. Web. 16 Dec. 2011. © 2011 American Chemical Society
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