Ni-catalyzed enantio- stereoselective synthesis of chiral chromans with quaternary allylic siloxanes and their antitumor activity

30 May 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Nickel-catalyzed efficient asymmetric synthesis of chiral chromans with quaternary allylic siloxanes and their antitumor activity is reported for the first time. A P-chiral monophosphine ligand (R)-AntPhos was found to be the ideal ligand to form a series of tertiary allylic siloxanes bearing chroman structures with excellent yields, enantioselectivities and E/Z selectivity using triethylsilane as the reductant. This reaction has a broad substrate scope and provides a practical way to synthesize useful chroman derivatives with chiral tertiary allylic alcohols. Up to 69 examples were successfully established with this method. A series of 3-hydroxychroman derivatives were obtained and tested for anti-tumor activity. Number of compounds showed good anti-tumor activity, less toxicity to reference cell, and specificity to different cancer cells, which could be new anticancer leading compounds. The configuration and substituent of the 3-hydroxychromans has big effects for their anti-tumor activity. Further study on structure-activity relationships of these 3-hydroxychromans is under investigation to discover new anti-cancer drugs.


Ni-catalyzed Reductive Cyclization
Asymmetric Catalytic Synthesis
Chiral Chromans with Quaternary Allylic Siloxanes
Antitumor Activity

Supplementary materials

Methods and procedures, HPLC, NMR


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