期刊
TETRAHEDRON
卷 69, 期 27-28, 页码 5702-5709出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.01.062
关键词
Asymmetric catalysis; Fluorination; Aziridine opening; Cooperative catalysis; beta-Fluoroamine
资金
- Princeton University
- NSF [CAREER-1148750]
- ACS Division of Organic Chemistry
- Pfizer
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1148750] Funding Source: National Science Foundation
The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans beta-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with k(rel)=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine. (C) 2013 Elsevier Ltd. All rights reserved.
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