Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 14-15, Pages 2678-2682Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200344
Keywords
allylic substitution; cycloaddition; heterocycles; quinone monoketals; regioselectivity
Categories
Funding
- NNSFC [21172031/21072027/20972029]
- NENU [10JCXK009, 10SSXT140]
- State Key Laboratory of Fine Chemicals [KF1003]
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A highly regioselective allylic substitution of quinone monoketals with a-oxoketene dithioacetals is achieved under the catalysis of only tin tetrachloride (1 mol%). The advantages of the reaction, including its simplicity, rapidity, low catalyst loading of inexpensive tin tetrachloride, mild conditions and; in particular, the regiospecificity, is proposed to be due to a pseudo-intramolecular process. This new synthetic method provides a facile [3+2]?cycloaddition route to benzofurans and is highlighted by the synthesis of coumestans.
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