Diastereoselective Au-Catalyzed Allene Cycloisomerizations to Highly Substituted Cyclopentenes

Site- and regiocontrolled Au-catalyzed allene carbocyclizations furnish highly substituted cyclopentenes in >1:1 dr. Significant substitution on the substrate is tolerated, with potential to install five contiguous stereocenters after alkene functionalization. Major challenges include identifying...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 13; pp. 3394 - 3397
Main Authors Reeves, Ryan D, Phelps, Alicia M, Raimbach, William A. T, Schomaker, Jennifer M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.07.2017
Amer Chemical Soc
Subjects
Alkadienes
Chemistry
Chemistry, Organic
Cyclopentanes
Gold - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
GOLD
DESIGN
DICARBONYL-COMPOUNDS
CHIRALITY TRANSFER
5-ENDO-DIG CARBOCYCLIZATION
COMPLEXES
COPPER
DERIVATIVES
CYCLIZATION
CONIA-ENE REACTION
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Summary:Site- and regiocontrolled Au-catalyzed allene carbocyclizations furnish highly substituted cyclopentenes in >1:1 dr. Significant substitution on the substrate is tolerated, with potential to install five contiguous stereocenters after alkene functionalization. Major challenges include identifying a Au/Cu catalyst that controls both the relative rates of allene epimerization/cyclization and the facial selectivity in addition of a metal enolate to the allene. Experiments to achieve stereodivergent cyclizations and transform key cyclopentenes into useful synthetic building blocks are described.
Bibliography:NIH RePORTER
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content type line 23
PPG Industries, Inc. Pittsburgh, PA 15222.
Present Address
Jennifer M. Schomaker: 0000-0003-1329-950X
ORCID
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01350