Journal
ORGANIC LETTERS
Volume 20, Issue 1, Pages 146-149Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03502
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Funding
- National Natural Science Foundation of China [21602089]
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A diversity-oriented synthesis of useful spirocyclic pyrrolidines was successfully accomplished via late-stage cascade reactions of o-succinimide-substituted benzaldehydes. A catalytic amount of aniline as a transient directing group was efficient for the ruthenium-catalyzed ortho-C(sp(2))-H alkylation of benzaldehyde with maleimide. The in situ formed imine overrided a series of other traditional directing groups with excellent site selectivities. More importantly, only 0.5 mol % of ruthenium catalyst was sufficient for a 100 mmol scale-up reaction without column chromatography purification.
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