Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 12, Pages 3520-3527Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304003
Keywords
allenes; diastereoselectivity; domino reactions; fused-ring systems; phospines; sequential annulation
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Funding
- National Natural Science Foundation of China [21172115, 20972076]
- Research Fund for the Doctoral Program of Higher Education of China [20120031110002]
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A novel strategy that involves phosphine-catalyzed sequential [2+3] and [3+2] annulation reactions was developed. In this domino reaction, -substituted allenoates were used as novel C-4 synthons, and the bicyclic cyclopenta[b]dihydrofuran derivatives were produced in good to excellent diastereoselectivities and yields under mild conditions. Furthermore, preliminary studies on an asymmetric variant of this reaction proceeded with moderate enantioselectivity.
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