Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of gamma-Thioesters
Name
nihms187016-1.pdf
Size
425.17 KB
Format
Adobe PDF
Checksum (MD5)
16623f2155d4489c6e1ef5d65c332dd1
Author(s)
Sun, Jianwei
Fu, Gregory C.
Date Issued
March 2010
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Citation
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
Version
Author's final manuscript
Abstract
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.
Description
Supporting Information Available: Experimental procedures and compound characterization data. This material is available free of charge via the Internet at http://pubs.acs.org.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/ja101251d
