Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 46, Pages 16506-16509Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10786
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Funding
- JSPS [26220802, 17H06451]
- Grants-in-Aid for Scientific Research [17K05824, 26220802, 17H06451] Funding Source: KAKEN
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Stereodivergent asymmetric catalysis is an important technology that can allow efficient access to various stereoisomers of a given product with multiple stereocenters from the same set of starting materials, but its application to the synthesis of a highly strained cyclopropane compound has remained unexplored to date. We report here the first diastereodivergent enantioselective synthesis of bicyclic aminocyclopropanes by lanthanum-catalyzed asymmetric carboamination/annulation of cydopropenes with aminoalkenes. This protocol features 100% atom efficiency, good yield (up to 90%), and high chemo-(up to >20:1) and stereoselectivity (up to >20:1 dr and 99% ee), constituting a unique route for the efficient synthesis of two different diastereoisomers of a given chiral bicyclic aminocyclopropane compound.
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