Stereodefined N,O-acetals: Pd-catalyzed Synthesis from Homopropargylic Amines and Utility in the Flexible Synthesis of 2,6-Substituted Piperidines
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- Title
- Stereodefined N,O-acetals: Pd-catalyzed Synthesis from Homopropargylic Amines and Utility in the Flexible Synthesis of 2,6-Substituted Piperidines
- Authors
- Kim, H; Rhee, YH
- Date Issued
- 2012-03-07
- Publisher
- American chemical society
- Abstract
- We developed a conceptually new synthetic strategy which exploits the stereochemical information of labile acyclic N,O-acetals. The key to this strategy, chemo- and stereoselective synthesis of N,O-acetals, was achieved by the Pd-catalyzed addition of sulfonyl-protected homopropargylic amines to alkoxyallene. The N,O-acetals generated in this way were combined with Au-catalyzed cycloisomerization to give an access to 2,6-disubstituted piperidines with stereochemical flexibility.
- Keywords
- ASYMMETRIC ALLYLIC ALKYLATION; GOLD(I)-CATALYZED INTRAMOLECULAR CARBOALKOXYLATION; RING-CLOSING METATHESIS; N-ACYLIMINIUM ION; INTERMOLECULAR HYDROAMINATION; ALLENES; GOLD; ALKYNES; ACIDS; ALKOXYALLENES
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/16490
- DOI
- 10.1021/JA2116298
- ISSN
- 0002-7863
- Article Type
- Article
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, no. 9, page. 4011 - 4014, 2012-03-07
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