Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 23, Pages 4464-4469Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800870
Keywords
organocatalysts; benzoxazinone; cyclic imine; Mannich reaction; &-proline; alpha-amino acid; regioselectivity
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Funding
- National Research Foundation of Korea - Korea Government (MSIP) [MRC 2017R1A5A2015541]
- International Science and Business Belt Program through the Ministry of Science, ICT and Future Planning [2017K000490]
- Basic Science Research Program through the Ministry of Science, ICT and Future Planning [2017R1D1A1B03]
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In this study, we have developed solvent-controlled regioselective Mannich reaction of cyclicimines (benzoxazinones) with various ketones by using &-proline as catalyst to afford Mannich products in high yields with excellent enantio- and diastereoselectivity. The unsymmetrical ketones produced the linear isomer as the major product in chloroform solvent. On contrary, using the DMSO solvent favoured the formation of branch isomer product with excellent enantio- and diastereoselectivity. The aromatic auxiliary was successfully removed and afforded N-protected chiral amino acid derivative.
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