Journal
ORGANIC LETTERS
Volume 24, Issue 25, Pages 4620-4624Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01736
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Funding
- National Natural Science Foundation of China [21772138, 21672157]
- Natural Science Foundation of Jiangsu Province
- project of scientific and technologic infrastructure of Suzhou [SZS201708]
- PAPD
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A catalyst-free [1+2+3] cycloaddition/N-N bond cleavage sequential reaction was developed to access spiroindolines with syn-stereoselectivity by utilizing an underexplored reaction mode of C,N-cyclic azomethine imines. Experimental results and DFT calculations identified peroxide and ethereal solvent as triggers for the reaction, initiating hydrogen abstraction and subsequent N-N bond cleavage.
By utilizing an underexplored reaction mode of C,N-cyclic azomethine imines, a catalyst-free [1+2+3] cycloaddition/N-N bond cleavage sequential reaction for accessing spiroindolines with syn-stereoselectivity was developed. On the basis of experimental results and DFT calculations, peroxide and ethereal solvent were identified to trigger the hydrogen abstraction of the unstable [1+2+3] cycloaddition adducts, followed by homolytic cleavage of the N-N bond and hydrogen absorption.
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