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- Title
Synergistic Kinetic Resolution and Asymmetric Propargyl Claisen Rearrangement for the Synthesis of Chiral Allenes.
- Authors
Liu, Yangbin; Liu, Xiaohua; Hu, Haipeng; Guo, Jing; Xia, Yong; Lin, Lili; Feng, Xiaoming
- Abstract
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.
- Subjects
ALLENE; DIOLEFINS; KINETIC resolution; CLAISEN rearrangement; ETHERS
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 12, p4122
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201511776