期刊
ORGANIC LETTERS
卷 20, 期 5, 页码 1333-1337出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00067
关键词
-
资金
- NIH [GM087605]
- Boehringer Ingelheim Pharmaceuticals
Enantioselective synthesis of alpha-aryl and alpha-heteroaryl piperidines is reported. The key step is an iridium-catalyzed asymmetric hydrogenation of substituted N-benzylpyridinium salts. High levels of enantioselectivity up to 99.3:0.7 er were obtained for a range of alpha-heteroaryl piperidines. DFT calculations support an outersphere dissociative mechanism for the pyridinium reduction. Notably, initial protonation of the final enamine intermediate determines the stereochemical outcome of the transformation rather than hydride reduction of the resultant iminium intermediate.
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