Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis

Zhouli Hu, Chenlong Wei, Qianqian Shi, Xianfang Hong, Jinhua Liu, Xiangui Zhou, Jinna Han, Wei Cao, Ashis Kumar Gupta, Xiaoxiang Zhang, Donghui Wei (), Zhenqian Fu () and Wei Huang
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Zhouli Hu: Nanjing Tech University
Chenlong Wei: Nanjing Tech University
Qianqian Shi: Zhengzhou University
Xianfang Hong: Nanjing Tech University
Jinhua Liu: Nanjing Tech University
Xiangui Zhou: Nanjing Tech University
Jinna Han: Nanjing Tech University
Wei Cao: Nanjing Tech University
Ashis Kumar Gupta: Nanjing Tech University
Xiaoxiang Zhang: Nanjing Forestry University
Donghui Wei: Zhengzhou University
Zhenqian Fu: Nanjing Tech University
Wei Huang: Nanjing Tech University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Over the past decade, the catalysis of N-heterocyclic carbenes has achieved significant advances. In this area, aldehydes, enals, and esters, are commonly employed as starting materials through various catalytic activation modes. However, NHC-activated strategy of amide and its derivatives remains elusive. Described herein is the realization of asymmetric desymmetrization of N-Cbz glutarimides with alcohols through an imide C-N bond cleavage under NHC organocatalysis. A structurally diverse set of enantioenriched 4-amido esters is generated with acceptable yields and high enantioselectivities. This method features mild reaction conditions, excellent substrate scope, and excellent atom economy. DFT calculations have been performed to explore the detailed reaction mechanism and the origin of the enantioselectivity, which indicate that the strength of the C-H···O hydrogen bond and C–H⋯π interactions should be responsible for the stereoselectivity. The current strategy could open a door for efficient construction of (R)-Rolipram with excellent stereoselectivity.

Date: 2022
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DOI: 10.1038/s41467-022-31760-z

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