Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/148220
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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