beta-Oxidation of Ynamides into N,O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization
- Title
- beta-Oxidation of Ynamides into N,O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization
- Author
- 신승훈
- Keywords
- FORMAL 3+2 CYCLOADDITION; GOLD-CATALYZED ADDITION; SELECTIVE SYNTHESIS; CARBENES; ACCESS; ALKYNES; OXIRENE; IMINES; EPOXIDATIONS; GENERATION
- Issue Date
- 2019-11
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v. 21, no. 22, Page. 9009-9013
- Abstract
- Oxidation of ynamides by mCPBA led to βoxygenation and resulted in formation of carbonyl compounds with α-N,O-acetal functionality. These N,O-acetals are formed in high yields and can be stored indefinitely at room temperature. Yet, they can be activated by a chiral Brønsted acid and underwent an enantioselective transacetalization into a α-N,O-acetal. Subsequent diastereoselective transformations occurred with exceptional selectivity according to Felkin-Anh model.
- URI
- https://pubs.acs.org/doi/10.1021/acs.orglett.9b03411https://repository.hanyang.ac.kr/handle/20.500.11754/155368
- ISSN
- 1523-7060; 1523-7052
- DOI
- 10.1021/acs.orglett.9b03411
- Appears in Collections:
- COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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