Synthesis

Generally applicable organocatalytic tetrahydropyranylation of hydroxy functionalities with very low catalyst loading

M Kotke, PR Schreiner

Index: Kotke, Mike; Schreiner, Peter R. Synthesis, 2007 , # 5 p. 779 - 790

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Citation Number: 78

Abstract

Abstract This paper presents the first acid-free, organocatalytic tetrahydropyran and 2- methoxypropene protection of alcohols, phenols, and other ROH derivatives utilizing privileged N, N′-bis [3, 5-bis (trifluoromethyl) phenyl] thiourea and a polystyrene-bound analogue. The reactions are broadly applicably (also on preparative scale), in particular, to acid-sensitive substrates such as aldol products, hydroxy esters, acetals, silyl-protected ...