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Enantioselective construction of branched 1,3-dienyl substituted quaternary carbon stereocenters by asymmetric allenyl Claisen rearrangement.
- Source :
-
Chemical Communications . 10/14/2016, Vol. 52 Issue 80, p11963-11966. 4p. - Publication Year :
- 2016
-
Abstract
- The availability of enantiomerically enriched 1,3-dienyl substituted quaternary stereocenters is highly valuable for the synthesis of complex natural compounds. Despite great advances in the area of construction of alkenyl-substituted types, a general, practical catalytic system that works for enantioselective formation of 1,3-diene derivatives still remains to be developed. Herein, we disclose the first asymmetric Claisen rearrangement of allenyl vinyl ethers to access optically active β-ketoesters, containing branched 1,3-butadienyl substituted stereocenters. A variety of substrates bearing a range of useful functional groups were well tolerated, thus affording the corresponding products with excellent enantioselectivities (up to 99% ee) and high yields (up to 91%). [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 13597345
- Volume :
- 52
- Issue :
- 80
- Database :
- Academic Search Index
- Journal :
- Chemical Communications
- Publication Type :
- Academic Journal
- Accession number :
- 118419378
- Full Text :
- https://doi.org/10.1039/c6cc06481g