期刊
CHEM
卷 3, 期 6, 页码 979-990出版社
CELL PRESS
DOI: 10.1016/j.chempr.2017.10.008
关键词
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资金
- National Natural Science Foundation of China [21722203, 21572096, 21602098]
- Shenzhen special funds for the development of biomedicine, Internet, new energy, and new material industries [JCYJ20170412152435366, JCYJ20170307105638498]
Catalytic asymmetric diamination of alkenes is a highly attractive method for creating chiral vicinal diamines, which are ubiquitous in biologically active molecules and versatile ligands as well as organocatalysts. We report the use of O-acylhydroxylamines as dialkylaminyl radical precursors to trigger asymmetric diamination of alkene under Cu(I)/chiral phosphoric acid dual catalysis. This reaction allows for direct alkylamine incorporation and features high enantioselectivity, a broad substrate scope, wide functional-group tolerance, and mild reaction conditions, providing convenient and practical access to a wide range of highly enantio-enriched beta-alkylamine-containing pyrrolidines. We have also achieved asymmetric azidoamination of alkenes by using azidoiodinane as an azidyl radical precursor, offering a complementary method for preparing diverse chiral beta-amino pyrrolidines. The application of the resultant a-tertiary pyrrolidine-derived diamine was showcased to significantly promote the enantioselectivity of an asymmetric Michael reaction.
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