Synthesis of spiro [furan-3, 3′-indolin]-2′-ones by PET-catalyzed [3+ 2] reactions of spiro [indoline-3, 2′-oxiran]-2-ones with electron-rich olefins

L Wang, Z Li, L Lu, W Zhang

Index: Wang, Lihong; Li, Zhanshan; Lu, Lianhong; Zhang, Wei Tetrahedron, 2012 , vol. 68, # 5 p. 1483 - 1491

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Citation Number: 9

Abstract

An efficient procedure for the synthesis of spiro [furan-3, 3′-indolin]-2-ones and dispiro [cycloalkane-1, 2′-furan-3′, 3 ″-indolin]-2 ″-ones has been achieved in high yields and stereoselectivity by photoinduced electron transfer-catalyzed [3+ 2] reactions of substituted spiro [indoline-3, 2′-oxiran]-2-ones with olefins. The reactions proceed by ring opening of spiro [indoline-3, 2′-oxiran]-2-ones via Cβ–O bond cleavage and subsequent ...