Stereodivergent Access to Aliphatic Nitro Compounds Bearing Multi‐Contiguous Stereocenters via Sequential Catalysis

Herein, we report a highly efficient synthesis of aliphatic nitro compounds bearing multi-contiguous stereocenters in good yields (up to 72%) with excellent diastereo- and enantio-selectivities (up to 12:1 dr, and >99% ee) by combining copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to nitroalkenes with iridium-catalyzed asymmetric allylic substitution reaction. Stereodivergent construction of nonadjacent stereocenters (1,3-positions) has been achieved by combining two chiral catalysts with different enantiomers. By first introducing a chiral center at the β-position of the nitro group, highly diastereoselective control has been achieved in iridium-catalyzed allylic substitution reaction of prochiral nitro compounds.

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Publication Details

Journal
Advanced Science
Published
2026-02-03
DOI
https://doi.org/10.1002/advs.202519142
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Stereodivergent Access to Aliphatic Nitro Compounds Bearing Multi‐Contiguous Stereocenters via Sequential Catalysis

Chao Zheng, Jinghe Xie, Yi‐Ming Hou, Zhi‐Jie Wu et al.
Advanced Science
Asymmetric Synthesis and Catalysis
article

Stereodivergent Access to Aliphatic Nitro Compounds Bearing Multi‐Contiguous Stereocenters via Sequential Catalysis

Chao Zheng, Jinghe Xie, Yi‐Ming Hou, Zhi‐Jie Wu, Shu‐Li You
article en

Abstract

Herein, we report a highly efficient synthesis of aliphatic nitro compounds bearing multi-contiguous stereocenters in good yields (up to 72%) with excellent diastereo- and enantio-selectivities (up to 12:1 dr, and >99% ee) by combining copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to nitroalkenes with iridium-catalyzed asymmetric allylic substitution reaction. Stereodivergent construction of nonadjacent stereocenters (1,3-positions) has been achieved by combining two chiral catalysts with different enantiomers. By first introducing a chiral center at the β-position of the nitro group, highly diastereoselective control has been achieved in iridium-catalyzed allylic substitution reaction of prochiral nitro compounds.

Advanced ScienceVol. 13(14)
Shanghai Institute of Organic Chemistry (CN)
National Natural Science Foundation of China, Chinese Academy of Sciences, Science and Technology Commission of Shanghai Municipality
Openalex Percentile: Top 67%
Asymmetric Synthesis and Catalysis
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Stereodivergent Access to Aliphatic Nitro Compounds Bearing Multi‐Contiguous Stereocenters via Sequential Catalysis — Chao Zheng, Jinghe Xie, et al. · Advanced Science (2026) | TGRS Research Map | TGRS