Journal
ORGANIC LETTERS
Volume 21, Issue 17, Pages 6679-6683Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02280
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Funding
- National Research Foundation of Korea (NRF) - Korean government (MSIP) [NRF-2016R1A2B3007119, 2019R1A4A2001440]
- National Research Foundation of Korea [2019R1A4A2001440] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various alpha-aminonitriles and homoallylic amines were synthesized in high yield (up to 98%) with high to excellent enantioselectivity (up to 99% ee). A rational mechanistic model for the complex of COBI and aldimine is provided to account for these enantioselective reactions.
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