Synthesis and Application of New Chiral Phosphoric Acids Based on oxa-Spirocyclic Diphenol
- 1School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang 421001, China
Abstract
Chiral phosphoric acids (CPAs) are a highly versatile class of Brønsted acid catalysts. They have been employed in various challenging organic transformations. However, previously reported chiral phosphoric acids are still limited in variety. In this work, a new type of CPAs with different substitutions (27 examples) derived from the O-SPINOL scaffold was synthesized through 8 steps. The new type of CPAs were applied to the electrophilic amination of indoles bearing bulky substituents and exhibited high catalytic efficiency. Preliminary comparative experiments revealed that the chiral phosphoric acid derived from O-SPINOL gave better catalytic performance in terms of enantioselectivity than that derived from SPINOL in most examples. This new type of chiral phosphoric acids adds to and complements the existing pool of chiral phosphoric acid catalysts.
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BibTeX
@article{chen2026synthesis,
title = {{Synthesis and Application of New Chiral Phosphoric Acids Based on oxa-Spirocyclic Diphenol}},
author = {Jia-Jie Chen and Zhuo-Ting Chen and Peng Wang and Wen-Jing Wang and Li-Guo Shen and Zhi-Yuan Bai and Si-Hai Zhou and Zehua Yang and Ye-Hui Chen},
journal = {Molecules},
year = {2026},
month = oct,
doi = {10.3390/molecules31213858},
url = {https://www.mdpi.com/1420-3049/31/21/3858},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Synthesis and Application of New Chiral Phosphoric Acids Based on oxa-Spirocyclic Diphenol
AU - Jia-Jie Chen
AU - Zhuo-Ting Chen
AU - Peng Wang
AU - Wen-Jing Wang
AU - Li-Guo Shen
AU - Zhi-Yuan Bai
AU - Si-Hai Zhou
AU - Zehua Yang
AU - Ye-Hui Chen
PY - 2026
DA - 2026/10/26
JO - Molecules
DO - 10.3390/molecules31213858
UR - https://www.mdpi.com/1420-3049/31/21/3858
AB - Chiral phosphoric acids (CPAs) are a highly versatile class of Brønsted acid catalysts. They have been employed in various challenging organic transformations. However, previously reported chiral phosphoric acids are still limited in variety. In this work, a new type of CPAs with different substitutions (27 examples) derived from the O-SPINOL scaffold was synthesized through 8 steps. The new type of CPAs were applied to the electrophilic amination of indoles bearing bulky substituents and exhibited high catalytic efficiency. Preliminary comparative experiments revealed that the chiral phosphoric acid derived from O-SPINOL gave better catalytic performance in terms of enantioselectivity than that derived from SPINOL in most examples. This new type of chiral phosphoric acids adds to and complements the existing pool of chiral phosphoric acid catalysts.
SN - 1420-3049
ER -