期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 9, 期 -, 页码 2812-2820出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.316
关键词
catalysis; enantioselectivity; fluorine; gauche effect; organo; fluorine; Steglich rearrangement
资金
- WWU Munster
- ETH Zurich (Independent Investigator Research Award)
- Deutsche Forschungsgemeinschaft [DFG EXC 1003]
Fluorination often confers a range of advantages in modulating the conformation and reactivity of small molecule organocatalysts. By strategically introducing fluorine substituents, as part of a beta-fluoroamine motif, in a triazolium pre-catalyst, it was possible to modulate the behaviour of the corresponding N-heterocyclic carbene (NHC) with minimal steric alterations to the catalyst core. In this study, the effect of hydrogen to fluorine substitution was evaluated as part of a molecular editing study. X-ray crystallographic analyses of a number of derivatives are presented and the conformations are discussed. Upon deprotonation, the fluorinated triazolium salts generate catalytically active N-heterocyclic carbenes, which can then participate in the enantioselective Steglich rearrangement of oxazolyl carbonates to C-carboxyazlactones (e.r. up to 87.0: 13.0).
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