Formal Alkyne Aza-Prins Cyclization: Gold(I)-Catalyzed Cycloisomerization of Mixed N,O-Acetals Generated from Homopropargylic Amines to Highly Substituted Piperidines
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SCOPUS
- Title
- Formal Alkyne Aza-Prins Cyclization: Gold(I)-Catalyzed Cycloisomerization of Mixed N,O-Acetals Generated from Homopropargylic Amines to Highly Substituted Piperidines
- Authors
- Kim, C; Bae, HJ; Lee, JH; Jeong, W; Kim, H; Sampath, V; Rhee, YH
- Date Issued
- 2009-10-21
- Publisher
- AMER CHEMICAL SOC
- Abstract
- A new gold (I)-catalyzed cycloisomerization to access highly substituted piperidines has been developed. By combining a conceptually new way of generating iminium ions using cationic gold(I) complexes and an efficient cyclization reaction that can minimize a potentially competing aza-Cope rearrangement, the proposed reaction successfully circumvents a long-standing problem in the classical aza-Prins reaction. Synthetic utility of the catalytic reaction was demonstrated by a synthesis of optically active 2-alkyl-pipendin-4-one.
- Keywords
- GOLD CATALYSIS; INTRAMOLECULAR CARBOALKOXYLATION; AU CATALYSIS; PLATINUM; REARRANGEMENTS; ALKALOIDS; EPOXIDES; ENYNES; ACIDS
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/27785
- DOI
- 10.1021/JA906744R
- ISSN
- 0002-7863
- Article Type
- Article
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, no. 41, page. 14660 - 14661, 2009-10-21
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