Rhodium(II)-Catalyzed Alkyne Amination of Homopropargylic Sulfamate Esters: Stereoselective Synthesis of Functionalized Norcaradienes by Arene Cyclopropanation

A rhodium(II) catalyzed nitrene–alkyne cycloaddition of stereochemically well-defined homopropargylic ethers is followed by arene cyclopropanation to afford unique tetracyclic norcaradiene products bearing a cyclic sulfamate. Products from the arene cyclopropanation (Buchner reaction) can be convert...

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Bibliographic Details
Published in:Organic letters 2014-01, Vol.16 (1), p.74-77
Main Authors: Brawn, Ryan A, Zhu, Kaicheng, Panek, James S
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Amination
Catalysis
Cyclization
Cycloheptanes - chemical synthesis
Cycloheptanes - chemistry
Cyclopropanes - chemistry
Esters
Imines - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
Sulfonic Acids - chemistry
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Summary:A rhodium(II) catalyzed nitrene–alkyne cycloaddition of stereochemically well-defined homopropargylic ethers is followed by arene cyclopropanation to afford unique tetracyclic norcaradiene products bearing a cyclic sulfamate. Products from the arene cyclopropanation (Buchner reaction) can be converted to fused cycloheptatrienes via a ring enlarging electrocyclization after nucleophilic ring opening of the cyclic sulfamate ester.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403035g