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BF3-promoted synthesis of spiroindenyl heterocycles

✍ Scribed by Meng-Yang Chang; Chung-Han Lin; Yeh-Long Chen; Ru-Ting Hsu; Ching-Yao Chang

Book ID
104097733
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
1008 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

An easy and straightforward synthesis of spiroindenyl heterocycles by the repeated treatment of boron trifluoride etherate (BF 3 -OEt 2 ) is reported. The overall transformation from ketones 1 to spiro-fused indenes 3 proceeds via Wittig olefination, deconjugation, Grignard addition, and intramolecular electrophilic cyclization in moderate yields. It presents a novel rearrangement reaction catalyzed by boron trifluoride etherate and broadens the scope of application.

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