Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 10, Pages 5273-5278Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202013792
Keywords
diastereoselectivity; domino reactions; hydrogen autotransfer; indanones; spiro compounds
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Funding
- 1000-Youth Talents Plan
- NSFC [21702149]
- Wuhan University
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This study describes an unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio- and diastereoselectivity. Preliminary mechanistic studies suggest that indanones are formed through cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.
An unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes is described. The reaction features broad substrate scope and is tolerant of a variety of functional groups, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio- and diastereoselectivity. Preliminary mechanistic studies have shown that indanones are formed by the cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.
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