Ruthenium-Catalyzed Intramolecular Double Hydrofunctionalization of Alkynes. Synthesis of Spirocyclic Hemiaminal Ethers and Their Lewis Acid-Mediated Cleavage/Nucleophilic Addition

[RuCl2(p-cymene)]2/AgNO3-catalyzed intramolecular double hydrofunctionalization of internal alkynes having nitrogen and oxygen nucleophilic groups at appropriate positions provided a series of spirocyclic hemiaminal ether derivatives in good to excellent yields. The product spiro-hemiaminal ethers u...

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Published inJournal of organic chemistry Vol. 86; no. 9; pp. 6674 - 6697
Main Authors Nishimura, Kazuma, Hanzawa, Ryohei, Sugai, Tomoya, Fuwa, Haruhiko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.05.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFORMATION
MITSUNOBU REACTION
SPIROAMINALS
STRUCTURAL ELUCIDATION
IONS
RADICALS
LACTAMS
MARINEOSINS
SPIROKETALS
AMIDES
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Summary:[RuCl2(p-cymene)]2/AgNO3-catalyzed intramolecular double hydrofunctionalization of internal alkynes having nitrogen and oxygen nucleophilic groups at appropriate positions provided a series of spirocyclic hemiaminal ether derivatives in good to excellent yields. The product spiro-hemiaminal ethers underwent Lewis acid-mediated chemoselective cleavage, and in situ-generated iminium/oxocarbenium ions could be trapped with nucleophiles to afford a range of nitrogen and oxygen heterocycles.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00443