Journal
TETRAHEDRON
Volume 66, Issue 11, Pages 1980-1989Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.01.073
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- 21st Century COE Program 'Knowledge Information Infrastructure for Genome Science'
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The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.
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