Tetrahedron Letters

N-Acyl 1, 5-diazabicyclo [4.3. 0] non-5-ene (DBN) tetraphenylborate salts as O-acylating agents

JE Taylor, JMJ Williams, SD Bull

Index: Taylor, James E.; Williams, Jonathan M.J.; Bull, Steven D. Tetrahedron Letters, 2012 , vol. 53, # 32 p. 4074 - 4076

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Citation Number: 7

Abstract

Air-stable and crystalline N-acyl DBN tetraphenylborate salts have been shown to be effective O-acylating agents, reacting with both primary and secondary alcohols to give the corresponding esters in good yields. In the case of diols, the N-acyl DBN· BPh4 salts have been shown to acylate regioselectively the primary alcohol functionality in the presence of a secondary alcohol. The DBN hydrotetraphenylborate side product can be readily removed ...