期刊
ACS CATALYSIS
卷 12, 期 23, 页码 14592-14600出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c04571
关键词
asymmetric catalysis; enantioselective hydrogermylation; beta-germyl alpha-amino acids; copper catalysis; Cu-Ge intermediate
资金
- National Natural Science Foundation of China
- Guangdong Provincial Key Laboratory of Catalysis
- Shenzhen Science and Technology Innovation Committee
- Stable Support Plan Program of Shenzhen Natural Science Fund
- [22122102]
- [22101120]
- [22271134]
- [2020B121201002]
- [JCYJ20190809142809370]
- [20200925152450004]
A copper-catalyzed asymmetric synthesis method has been developed to efficiently prepare chiral beta-germyl alpha-amino acid derivatives, and mechanistic studies have revealed the reaction process. Subsequent transformations yielded a series of germanium-containing functional molecules with potential utility.
A copper-catalyzed asymmetric synthesis of unnatural beta-germyl alpha-amino acids is developed. This process undergoes an intermolecular enantioselective hydrogermylation of dehydroalanines with dihydrogermanes and trihydrogermanes, giving access to a variety of chiral beta-germyl alpha-amino acid derivatives in decent yields with good to excellent enantioselectivities. Mechanistic studies indicate that a [Cu-Ge] species is the key intermediate in this hydrogermylation process, rather than the [Cu-H] species which are commonly generated in the copper-catalyzed hydrosilylation reactions. Further stereospecific transformation of the protected beta-germyl alpha-amino acids delivered a number of enantioenriched germanium-containing functional molecules that could be potentially useful in many areas.
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