期刊
TETRAHEDRON
卷 69, 期 36, 页码 7618-7626出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.05.011
关键词
Oxidation; Fragment coupling; Heterocycles; Chiral counterions; Enantioselectivity
资金
- NIGMS NIH HHS [R01 GM062924, F32 GM018311, P50 GM067082] Funding Source: Medline
Chromenes, isochromenes, and benzoxathioles react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form stable aromatic cations that react with a range of nucleophiles. These oxidative fragment coupling reactions provide rapid access to structurally diverse heterocycles. Conducting the reactions in the presence of a chiral Bronsted acid results in the formation of an asymmetric ion pair that can provide enantiomerically enriched products in a rare example of a stereoselective process resulting from the generation of a chiral electrophile through oxidative carbon hydrogen bond cleavage. (C) 2013 Elsevier Ltd. All rights reserved.
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