Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 3, Pages 1238-1242Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909158
Keywords
[4+3] cyclization; asymmetric catalysis; chiral azepines; cycloaddition; palladium
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Funding
- National Natural Science Foundation of China [21971062]
- Fundamental Research Funds for the Central Universities
- China Postdoctoral Science Foundation [2018M632037]
- Shanghai Sailing Program [18YF140560]
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The palladium-catalyzed asymmetric [4+3] cyclization of trimethylenemethane donors with benzofuran-derived azadienes furnishes chiral benzofuro[3,2-b]azepine frameworks in high yields (up to 98 %) with exclusive regioselectivities and excellent stereoselectivities (up to >20:1 d.r., >99 % ee). This catalytic asymmetric [4+3] cyclization of Pd-trimethylenemethane can enrich the arsenal of Pd-TMM reactions in organic synthesis. In addition, this strategy provides an alternative approach to chiral azepines by a transition-metal-catalyzed asymmetric [4+3] cyclization.
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