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Title: | Access to allene-containing molecules via enantioselective reactions of azolium cumulenolate intermediates | Authors: | Xie, Yongtao Yang, Xing Xu, Jun Chai, Huifang Liu, Hongxia Zhang, Junmin Song, Jun Gao, Yuan Jin, Zhicao Chi, Robin Yonggui |
Keywords: | Science | Issue Date: | 2021 | Source: | Xie, Y., Yang, X., Xu, J., Chai, H., Liu, H., Zhang, J., Song, J., Gao, Y., Jin, Z. & Chi, R. Y. (2021). Access to allene-containing molecules via enantioselective reactions of azolium cumulenolate intermediates. Angewandte Chemie International Edition, 60(27), 14817-14823. https://dx.doi.org/10.1002/anie.202102177 | Journal: | Angewandte Chemie International Edition | Abstract: | Azolium cumulenolates are a special type of intermediates in N-heterocyclic carbene catalysis. They contain elongated linear structures with three contiguous C=C bonds and sterically unhindered α-carbon. These structure features make it difficult to develop enantioselective reactions for these intermediates. Here we disclose the first carbene-catalyzed highly enantioselective addition reactions of azolium cumulenolates. The reaction starts with alkynals as the precursors for azolium cumulenolate intermediates that undergo enantioselective addition to activated ketones. From the same set of substrates, both allene and spirooxindole products can be obtained with high yields and excellent enantioselectivities. The allene moieties in our optically enriched products carry rich reactivities and can be transformed to diverse molecules. The spirooxindole scaffolds in our products are important structural motifs in natural products and medicines. | URI: | https://hdl.handle.net/10356/148220 | ISSN: | 1521-3773 | DOI: | 10.1002/anie.202102177 | Rights: | This is the peer reviewed version of the following article: Xie, Y., Yang, X., Xu, J., Chai, H., Liu, H., Zhang, J., Song, J., Gao, Y., Jin, Z. & Chi, R. Y. (2021). Access to allene-containing molecules via enantioselective reactions of azolium cumulenolate intermediates. Angewandte Chemie International Edition, 60(27), 14817-14823. https://dx.doi.org/10.1002/anie.202102177, which has been published in final form at https://doi.org/10.1002/anie.202102177. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. | Fulltext Permission: | embargo_20220625 | Fulltext Availability: | With Fulltext |
Appears in Collections: | SPMS Journal Articles |
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Access to allene-containing molecules via enantioselective reactions of azolium cumulenolate intermediates.pdf Until 2022-06-25 | 1.14 MB | Adobe PDF | Under embargo until Jun 25, 2022 |
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