Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations
5 p.
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2017
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sg-ntu-dr.10356-819752023-02-28T19:31:51Z Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations Wu, Xingxing Hao, Lin Zhang, Yuexia Rakesh, Maiti Reddi, Rambabu N. Yang, Song Song, Bao-An Chi, Yonggui Robin School of Physical and Mathematical Sciences Lactones Heterocycles 5 p. A carbene-catalyzed intermolecular C−N bond formation, which initiates a highly selective cascade reaction for the synthesis of pyrrolidine fused β-lactones, is disclosed. The nitrogen-containing bicyclic β-lactone products are obtained with good yields and excellent stereoselectivities. Synthetic transformations of the reaction products into useful functional molecules, such as amino catalysts, can be efficiently realized under mild reaction conditions. Mechanistically, this study provides insights into modulating the reactivities of heteroatoms, such as nitrogen atoms, in challenging carbene-catalyzed asymmetric carbon–heteroatom bond-forming reactions. NRF (Natl Research Foundation, S’pore) MOE (Min. of Education, S’pore) Accepted version 2017-04-24T06:02:18Z 2019-12-06T14:44:04Z 2017-04-24T06:02:18Z 2019-12-06T14:44:04Z 2017 2017 Journal Article Wu, X., Hao, L., Zhang, Y., Rakesh, M., Reddi, R. N., Yang, S., et al. (2017). Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations. Angewandte Chemie International Edition, 56(15), 4201-4205. 1433-7851 https://hdl.handle.net/10356/81975 http://hdl.handle.net/10220/42294 10.1002/anie.201700045 197965 en Angewandte Chemie International Edition © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the author created version of a work that has been peer reviewed and accepted for publication by Angewandte Chemie International Edition, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1002/anie.201700045]. application/pdf |
| institution |
Nanyang Technological University |
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NTU Library |
| continent |
Asia |
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Singapore Singapore |
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NTU Library |
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DR-NTU |
| language |
English |
| topic |
Lactones Heterocycles |
| spellingShingle |
Lactones Heterocycles Wu, Xingxing Hao, Lin Zhang, Yuexia Rakesh, Maiti Reddi, Rambabu N. Yang, Song Song, Bao-An Chi, Yonggui Robin Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations |
| description |
5 p. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Wu, Xingxing Hao, Lin Zhang, Yuexia Rakesh, Maiti Reddi, Rambabu N. Yang, Song Song, Bao-An Chi, Yonggui Robin |
| format |
Article |
| author |
Wu, Xingxing Hao, Lin Zhang, Yuexia Rakesh, Maiti Reddi, Rambabu N. Yang, Song Song, Bao-An Chi, Yonggui Robin |
| author_sort |
Wu, Xingxing |
| title |
Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations |
| title_short |
Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations |
| title_full |
Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations |
| title_fullStr |
Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations |
| title_full_unstemmed |
Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations |
| title_sort |
construction of fused pyrrolidines and β-lactones by carbene-catalyzed c−n, c−c, and c−o bond formations |
| publishDate |
2017 |
| url |
https://hdl.handle.net/10356/81975 http://hdl.handle.net/10220/42294 |
| _version_ |
1759855639153082368 |