Asymmetric synthesis of all-carbon quaternary stereocenters via desymmetrization of 2,2-disubstituted 1,3-propanediols
Journal of the American Chemical Society, ISSN: 0002-7863, Vol: 133, Issue: 6, Page: 1772-1774
2011
- 69Citations
- 29Captures
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Metrics Details
- Citations69
- Citation Indexes69
- CrossRef69
- 68
- Captures29
- Readers29
- 29
Article Description
A novel enantioselective desymmetrization of 2,2-disubstituted 1,3-propanediols has been established to generate all-carbon quaternary stereocenters, which has been implemented with BzCl and EtN in the presence of Pybox(6)-CuCl complex in CHCl or PhMe at 78°C. While all the cyanide-comprising diols were desymmetrized with superb enantioselectivity (higher than 98% ee), the stereoinduction of the other substrates greatly depends on the size difference between the two substituents at the 2-position. When the size difference becomes larger, the corresponding substrates tend to engender enhanced enantioselectivity (up to 99% ee). © 2011 American Chemical Society.
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