Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/148221
Title: Carbene-catalyzed enantioselective aldol reaction : post-aldol stereochemistry control and formation of quaternary stereogenic centers
Authors: Yang, Xing
Majhi, Pankaj Kumar
Chai, Huifang
Liu, Bin
Sun, Jun
Liu, Ting
Liu, Yonggui
Zhou, Liejin
Xu, Jun
Liu, Jiawei
Wang, Dongdong
Zhao, Yanli
Jin, Zhichao
Chi, Robin Yonggui
Keywords: Science::Chemistry
Issue Date: 2021
Source: Yang, X., Majhi, P. K., Chai, H., Liu, B., Sun, J., Liu, T., Liu, Y., Zhou, L., Xu, J., Liu, J., Wang, D., Zhao, Y., Jin, Z. & Chi, R. Y. (2021). Carbene-catalyzed enantioselective aldol reaction : post-aldol stereochemistry control and formation of quaternary stereogenic centers. Angewandte Chemie International Edition, 133(1), 161-167. https://dx.doi.org/10.1002/anie.202008369
Journal: Angewandte Chemie International Edition
Abstract: The dominated approaches for asymmetric aldol reactions have primarily focused on the aldol carbon-carbon bond-forming events. Here we postulate and develop a new catalytic strategy that seeks to modulate the reaction thermodynamics and control the product enantioselectivities via post-aldol processes. Specifically, an NHC catalyst is used to activate a masked enolate substrate (vinyl carbonate) to promote the aldol reaction in a non-enantioselective manner. This reversible aldol event is subsequently followed by an enantioselective acylative kinetic resolution that is mediated by the same (chiral) NHC catalyst without introducing any additional substance. This post-aldol process takes care of the enantioselectivity issues and drives the otherwise reversible aldol reaction toward a complete conversion. The acylated aldol products bearing quaternary/tetrasubstituted carbon stereogenic centers are formed in good yields and high optical purities.
URI: https://hdl.handle.net/10356/148221
ISSN: 1521-3773
DOI: 10.1002/anie.202008369
Rights: This is the peer reviewed version of the following article: Yang, X., Majhi, P. K., Chai, H., Liu, B., Sun, J., Liu, T., Liu, Y., Zhou, L., Xu, J., Liu, J., Wang, D., Zhao, Y., Jin, Z. & Chi, R. Y. (2021). Carbene-catalyzed enantioselective aldol reaction : post-aldol stereochemistry control and formation of quaternary stereogenic centers. Angewandte Chemie International Edition, 133(1), 161-167. https://dx.doi.org/10.1002/anie.202008369 , which has been published in final form at https://doi.org/10.1002/ange.202008369. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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