Copper(I)-catalyzed diastereo- and enantio-selective construction of optically pure exocyclic allenes

Cheng-Yu He, Yun-Xuan Tan, Xin Wang, Rui Ding, Yi-Fan Wang, Feng Wang, Dingding Gao (), Ping Tian () and Guo-Qiang Lin ()
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Cheng-Yu He: Shanghai University of Traditional Chinese Medicine
Yun-Xuan Tan: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Xin Wang: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Rui Ding: Shanghai University of Traditional Chinese Medicine
Yi-Fan Wang: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Feng Wang: Shanghai University of Traditional Chinese Medicine
Dingding Gao: Shanghai University of Traditional Chinese Medicine
Ping Tian: Shanghai University of Traditional Chinese Medicine
Guo-Qiang Lin: Shanghai University of Traditional Chinese Medicine

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Among about 150 identified allenic natural products, the exocyclic allenes constitute a major subclass. Substantial efforts are devoted to the construction of axially chiral allenes, however, the strategies to prepare chiral exocyclic allenes are still rare. Herein, we show an efficient strategy for the asymmetric synthesis of chiral exocyclic allenes with the simultaneous control of axial and central chirality through copper(I)-catalyzed asymmetric intramolecular reductive coupling of 1,3-enynes to cyclohexadienones. This tandem reaction exhibits good functional group compatibility and the corresponding optically pure exocyclic allenes bearing cis-hydrobenzofuran, cis-hydroindole, and cis-hydroindene frameworks, are obtained with high yields (up to 99% yield), excellent diastereoselectivities (generally >20:1 dr) and enantioselectivities (mostly >99% ee). Furthermore, a gram-scale experiment and several synthetic transformations of the chiral exocyclic allenes are also presented.

Date: 2020
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DOI: 10.1038/s41467-020-18136-x

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