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research article

Accessing Carbon, Boron and Germanium Spiro Stereocentres in a Unified Catalytic Enantioselective Approach

Cao, Yi-Xuan  
•
Chauvin, Anne-Sophie  
•
Tong, Shuo
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June 12, 2025
Nature Catalysis

Achieving substrate generality in asymmetric catalysis remains a long-standing goal, particularly for the selective construction of chiral heteroatoms. Compared with carbon, sulfur, phosphorus and silicon stereogenic centres, methods for the construction of their boron and germanium congeners remain very scarce. Chiral (hetero) spirocycles are of relevance in several research domains. Methods effective for constructing carbon-centred chiral spirocycles do not translate to boron and germanium, leaving these chiral centres unexplored. We describe a unified strategy for constructing carbon, boron and germanium-centred chiral spirocyclic skeletons via enantioselective hetero [2+2+2] cycloaddition of a bis-alkyne with a nitrile. A chiral designer Ni(0) N-heterocyclic carbene complex enables the required long-range enantioinduction. The resulting enantio-enriched spirocycles feature a pyridine motif, making them exploitable for ligand design and functional materials featuring attractive photophysical and chiroptical properties.

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Type
research article
DOI
10.1038/s41929-025-01352-3
Web of Science ID

WOS:001507505300001

Author(s)
Cao, Yi-Xuan  

École Polytechnique Fédérale de Lausanne

Chauvin, Anne-Sophie  

École Polytechnique Fédérale de Lausanne

Tong, Shuo

Tsinghua University

Alama, Layth

École Polytechnique Fédérale de Lausanne

Cramer, Nicolai  

École Polytechnique Fédérale de Lausanne

Date Issued

2025-06-12

Publisher

NATURE PORTFOLIO

Published in
Nature Catalysis
Subjects

CYCLOADDITION

•

CONSTRUCTION

•

Science & Technology

•

Physical Sciences

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCS  
LCSA  
FunderFunding(s)Grant NumberGrant URL

Swiss National Science Foundation (SNSF)

Ni3;Ni4

EPFL

180544

NCCR Catalysis

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Available on Infoscience
June 19, 2025
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/251438
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