The tert-Butylsulfinamide Lynchpin in Transition-Metal-Mediated Multiscaffold Library Synthesis

A unified synthetic approach to diverse polycyclic scaffolds has been developed using transition-metal-mediated cycloaddition and cyclization reactions of enynes and diynes. The tert-butylsulfinamide group has been identified as a particularly versatile lynchpin in these reactions, with a reactivity...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 9; pp. 2084 - 2087
Main Authors Bauer, Renato A., DiBlasi, Christine M., Tan, Derek S.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.05.2010
Amer Chemical Soc
Subjects
Amides - chemistry
Chemistry
Chemistry, Organic
Cyclization
Magnetic Resonance Spectroscopy
Physical Sciences
Science & Technology
Transition Elements - chemistry
CATALYZED ASYMMETRIC HYDROGENATION
SULFINIMINES
DIVERSITY-ORIENTED SYNTHESIS
REAGENTS
SMALL MOLECULES
STRATEGY
2+2+2 CYCLOADDITION
SKELETAL DIVERSITY
ARYLBORONIC ACIDS
IMINE LIGANDS
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Summary:A unified synthetic approach to diverse polycyclic scaffolds has been developed using transition-metal-mediated cycloaddition and cyclization reactions of enynes and diynes. The tert-butylsulfinamide group has been identified as a particularly versatile lynchpin in these reactions, with a reactivity profile uniquely suited for efficient, stereoselective substrate synthesis and downstream transformations. This approach provides 10 distinct, functionalized scaffold classes related to common core structures in alkaloid and terpenoid natural products.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol100574y