Tetrahedron

A systematic study of two complementary protocols allowing the general, mild and efficient deprotection of N-pivaloylindoles

M Ruiz, JD Sánchez, P López-Alvarado, JC Menéndez

Index: Ruiz, Miriam; Sanchez, J. Domingo; Lopez-Alvarado, Pilar; Menendez, J. Carlos Tetrahedron, 2012 , vol. 68, # 2 p. 705 - 710

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Citation Number: 5

Abstract

Two mild and general protocols for the high-yielding deprotection of indoles and related fused heterocyclic systems are described, involving either hydride transfer from LDA or hydrolysis by the DBU–water system. Both methods were shown to tolerate a wide variety of substituents and functional groups, but the hydrolytic one proved to be particularly general, being compatible with 2-alkyl substituents, aldehydes, ketones, carboxylic acids, halogens ...

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