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

• Published in: Organic 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
• Language: English
• 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

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.