β-Oxidation of Ynamides into N, O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization

Nguyen, Nguyen H.; Nguyen, Quynh H.; Biswas, Soumen; Patil, Dilip V.; Shin, Seunghoon

doi:10.1021/acs.orglett.9b03411

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β-Oxidation of Ynamides into N, O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization

Nguyen, Nguyen H.;
Nguyen, Quynh H.;
Biswas, Soumen;
Patil, Dilip V.;
Shin, Seunghoon

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12

초록

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.

키워드

FORMAL 3+2 CYCLOADDITION; GOLD-CATALYZED ADDITION; SELECTIVE SYNTHESIS; CARBENES; ACCESS; ALKYNES; OXIRENE; IMINES; EPOXIDATIONS; GENERATION

제목: β-Oxidation of Ynamides into N, O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization

저자: Nguyen, Nguyen H.; Nguyen, Quynh H.; Biswas, Soumen; Patil, Dilip V.; Shin, Seunghoon

DOI: 10.1021/acs.orglett.9b03411

발행일: 2019-11

유형: Article

저널명: Organic Letters

권: 21

호: 22

페이지: 9009 ~ 9013