Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 3, Issue 4, Pages 412-415Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201300244
Keywords
allenoates; [4+2] cycloaddition; ketimines; organocatalysis; tetrahydropyridines
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Funding
- CREST project of the Japan Science and Technology Corporation (JST)
- Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
- JST, Advance Catalytic Transformation Program for Carbon Utilization (ACT-C)
- JSPS
- Grants-in-Aid for Scientific Research [13J07348, 24106726, 24590009, 24105518] Funding Source: KAKEN
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Enantioselective organocatalytic synthesis of tetrahydropyridines bearing a chiral tetrasubstituted carbon stereogenic center has been achieved. The spiro-type monoaryl phosphine catalyst, (R)-SITCP, was found to promote the formal [4+2] cycloaddition of saccharin-derived ketimines and -methyl allenoate to afford the corresponding six-membered N-heterocycles in high yields and excellent regioselectivities with up to 93% ee.
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