金催化的通过手性转移合成手性环戊二烯基酯。
Gold-Catalyzed Synthesis of Chiral Cyclopentadienyl Esters via Chirality Transfer.
机构信息
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
Department of Chemistry, National Tsing-Hua University, Hsinchu 30013, Taiwan, Republic of China.
出版信息
Org Lett. 2020 Aug 21;22(16):6500-6504. doi: 10.1021/acs.orglett.0c02293. Epub 2020 Aug 10.
Abstract
Efficient access to chiral cyclopentadienyl esters from readily accessible chiral enynyl ester substrates is developed. Typically high levels of chirality transfer realized in this homogeneous gold catalysis are attributed to the intermediacy of a chiral bent allene gold complex. Cyclopentadienyl esters can be prepared in good yields and with excellent enantiomeric excesses. The synthetic utilities of the chiral cyclopentadienyl esters are demonstrated by the Diels-Alder reactions, fluorination, alkylation, and epoxidation without any notable erosion of enantiopurity.
摘要
从易得的手性烯炔酯底物中高效获得手性环戊二烯酯。在这种均相金催化中，通常可以实现高水平的手性转移，这归因于手性弯曲丙二烯金配合物的中间体。环戊二烯酯可以以良好的收率和优异的对映选择性制备。通过 Diels-Alder 反应、氟化、烷基化和环氧化反应证明了手性环戊二烯酯的合成实用性，而对映体纯度没有明显损失。
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