Au-Catalyzed Piperidine Synthesis via Tandem Acyloxy Migration/Intramolecular [3 + 2] Cycloaddition of Enynyl Esters

An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of many bioactive molecules.

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 24; pp. 6448 - 6451
Main Authors Zheng, Huaiji, Huo, Xing, Zhao, Changgui, Jing, Peng, Yang, Juan, Fang, Bowen, She, Xuegong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.12.2011
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Cyclization
Esters
Gold - chemistry
Molecular Structure
Physical Sciences
Piperidines - chemical synthesis
Piperidines - chemistry
Science & Technology
Stereoisomerism
ACTIVATION
GOLD CATALYSIS
EFFICIENT SYNTHESIS
PLATINUM
CYCLOISOMERIZATION
BOND
REARRANGEMENTS
CYCLIZATION
1,N-ENYNES
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Summary:An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of many bioactive molecules.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202746s