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Acid-free, organocatalytic acetalization

Mike Kotke - No affiliation found

2006/01/09 Full-length article DOI: 10.1016/j.tet.2005.09.079 Journal: Tetrahedron

Abstract:

AbstractThe acid-free, organocatalytic acetalization of various aldehydes and ketones with N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea is presented. The neutral, double hydrogen bonding thiourea catalyst can be used at very low loadings of 0.01–1 mol% at room temperature to furnish the respective acetals in 65–99% yield at turnover frequencies around 600 h−1. Acid-labile TBDMS-protected as well as unsaturated aldehydes can be converted efficiently into their acetals utilizing this very mild and highly practical method.