β-Oxidation of Ynamides into N, O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization
- Authors
- Nguyen, Nguyen H.; Nguyen, Quynh H.; Biswas, Soumen; Patil, Dilip V.; Shin, Seunghoon
- Issue Date
- Nov-2019
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.21, no.22, pp.9009 - 9013
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC LETTERS
- Volume
- 21
- Number
- 22
- Start Page
- 9009
- End Page
- 9013
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/146887
- DOI
- 10.1021/acs.orglett.9b03411
- ISSN
- 1523-7060
- Abstract
- Oxidation of ynamides by mCPBA led to beta-oxygenation and resulted in formation of carbonyl compounds with alpha-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 Bronsted acid and underwent an enantioselective transacetalization into a alpha-N,O-acetal. Subsequent diastereoselective transformations occurred with exceptional selectivity according to Felkin-Anh model.
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