Tetrahedron Letters

BF 3-promoted synthesis of spiroindenyl heterocycles

MY Chang, CH Lin, YL Chen, RT Hsu, CY Chang

Index: Chang, Meng-Yang; Lin, Chung-Han; Chen, Yeh-Long; Hsu, Ru-Ting; Chang, Ching-Yao Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3154 - 3158

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Citation Number: 5

Abstract

An easy and straightforward synthesis of spiroindenyl heterocycles by the repeated treatment of boron trifluoride etherate (BF3-OEt2) 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 ...

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