Issue 80, 2016

Enantioselective construction of branched 1,3-dienyl substituted quaternary carbon stereocenters by asymmetric allenyl Claisen rearrangement

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%).

Graphical abstract: Enantioselective construction of branched 1,3-dienyl substituted quaternary carbon stereocenters by asymmetric allenyl Claisen rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
08 Aug 2016
Accepted
07 Sep 2016
First published
19 Sep 2016

Chem. Commun., 2016,52, 11963-11966

Enantioselective construction of branched 1,3-dienyl substituted quaternary carbon stereocenters by asymmetric allenyl Claisen rearrangement

Y. Liu, H. Hu, L. Lin, X. Hao, X. Liu and X. Feng, Chem. Commun., 2016, 52, 11963 DOI: 10.1039/C6CC06481G

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