Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 12, Pages 4054-4058Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511776
Keywords
allenes; asymmetric catalysis; chirality transfer; Claisen rearrangement; kinetic resolution
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Funding
- National Natural Science Foundation of China [21432006, 21321061]
- Fok Ying Tung Education Foundation [141115]
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The asymmetric propargyl Claisen rearrangement provides a convenient entry to chiral allene motifs. Herein, we describe the development of a kinetic resolution and asymmetric rearrangement of racemic propargyl vinyl ethers. This transformation afforded chiral allene products along with the enantiomerically enriched substrate in good yields with excellent diastereo- and enantioselectivity. The complete chirality transfer and facially selective rearrangement enabled the simultaneous construction of an axially chiral allenic unit and a quaternary carbon stereocenter.
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