Diastereoselective Mukaiyama aldol reaction of (N-alkyl) isatins with 2-(trimethylsilyloxy)furan by using lanthanum triflate

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Abstract

An efficient vinylogous Mukaiyama aldol reaction (VMAR) of 2-(trimethylsilyloxy)furan with various (N-alkyl)isatins is described in the presence of lanthanum(III) triflates (5 mol %). The reaction proceeds rapidly and affords the corresponding 3-hydroxy-(5-oxo-2,5-dihydrofuran-2-yl)indolin-2- one in high yields with good diastereoselectivities (threo:erythro ratio up to ≤95:5). © 2011 Elsevier Ltd. All rights reserved.

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Meshram, H. M., Ramesh, P., Reddy, B. C., Sridhar, B., & Yadav, J. S. (2011). Diastereoselective Mukaiyama aldol reaction of (N-alkyl) isatins with 2-(trimethylsilyloxy)furan by using lanthanum triflate. Tetrahedron, 67(17), 3150–3155. https://doi.org/10.1016/j.tet.2011.02.033

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