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Synergistic Kinetic Resolution and Asymmetric Propargyl Claisen Rearrangement for the Synthesis of Chiral Allenes |
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| Authors: | Yangbin Liu Prof. Dr. Xiaohua Liu Haipeng Hu Jing Guo Yong Xia Dr. Lili Lin Prof. Dr. Xiaoming Feng |
| Affiliation: | 1. Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China;2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, China |
| 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. |
| Keywords: | allenes asymmetric catalysis chirality transfer Claisen rearrangement kinetic resolution |