Unique Divergent Reactivity of Boc-Protected Homopropargylic Alkoxyalkylamines in the Gold(I)-Catalyzed Domino Catalytic Reactions: Application to the Formal Synthesis of (-)-Pseudodistomin B
SCIE
SCOPUS
- Title
- Unique Divergent Reactivity of Boc-Protected Homopropargylic Alkoxyalkylamines in the Gold(I)-Catalyzed Domino Catalytic Reactions: Application to the Formal Synthesis of (-)-Pseudodistomin B
- Authors
- Lee, JH; Jeong, W; Rhee, YH
- Date Issued
- 2014-08
- Publisher
- GEORG THIEME VERLAG KG
- Abstract
- By using t-Boc-protected homopropargylic alkoxyalkylamines as substrates, the reactivity between the carboxylation-promoted and the alkoxylation-promoted domino processes in the gold-catalyzed reaction was systematically compared. Interestingly, the result varies significantly depending upon the structure of the alkynes and the nature of the phosphine ligands. The alkoxylation-induced pathway represents a new synthetic method towards 2,4,5-trisubstituted piperidines. A formal synthesis of (-)-pseudodistomin B based upon this interesting chemoselectivity was accomplished.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/12964
- DOI
- 10.1055/S-0033-1338639
- ISSN
- 0039-7881
- Article Type
- Article
- Citation
- SYNTHESIS-STUTTGART, vol. 46, no. 16, page. 2155 - 2160, 2014-08
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