期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 18, 页码 9181-9189出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo4014386
关键词
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资金
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CSD2007-00006, CTQ2007-65218, CTQ2011-24151]
- Generalitat Valenciana [PROMETEO/2009/039]
- Spanish Ministerio de Educacion for a predoctoral fellowship [AP-2008-00989]
Highly optically enriched, protected, nitrogenated heterocycles with different ring sizes have been synthesized by a very efficient methodology consisting of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)-haloimines followed by treatment with a base to promote an intramolecular nucleophilic substitution process. N-Protected aziridines, pyrrolidines, piperidines, and azepanes bearing aromatic, heteroaromatic, and aliphatic substituents have been obtained in very high yields and diastereomeric ratios up to >99:1. The free heterocycles can be easily obtained by a simple and mild desulfinylation procedure. Both enantiomers of the free heterocycles can be prepared with the same good results by changing the absolute configuration of the sulfur atom of the sulfinyl group.
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