Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality

We describe herein an intriguing method for the synthesis of biaryl aldehydes bearing both axial and central chirality through a desymmetric [3 + 2] cycloaddition reaction of activated isocyanides with prochiral biaryl dialdehydes under silver catalysis. This protocol features excellent enantioselec...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-04, Vol.59 (3), p.4487-449
Main Authors: Huang, Fen, Tao, Ling-Fei, Liu, Jiyong, Qian, Linghui, Liao, Jia-Yu
Format: Article
Language:English
Subjects:
Aldehydes
Chirality
Cycloaddition
Enantiomers
Functional groups
Synthesis
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Summary:We describe herein an intriguing method for the synthesis of biaryl aldehydes bearing both axial and central chirality through a desymmetric [3 + 2] cycloaddition reaction of activated isocyanides with prochiral biaryl dialdehydes under silver catalysis. This protocol features excellent enantioselectivity, 100% atom economy, good functional group compatibility, and operational simplicity. An unprecedented method for the synthesis of biaryl aldehydes bearing both axial and central chirality is presented.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc00708a