Tetrahedron Letters

An SN 2′ displacement approach to allenyl acetates

M Asikainen, W Lewis, AJ Blake, S Woodward

Index: Asikainen, Martta; Lewis, William; Blake, Alexander J.; Woodward, Simon Tetrahedron Letters, 2010 , vol. 51, # 49 p. 6454 - 6456

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Citation Number: 5

Abstract

Reaction of cuprates derived from R3MgBr/CuI/LiBr (R3= n-alkyl) with R1CCCH (O2CR2) 2 (R1= sp2 hybridised substituent, R2= mainly Me, alkyl, Ph) provides access to allenyl esters R1R3CCCH (O2CR2)(51–88%). Such species are not accessible via rearrangement of precursor propargylic R1R3C (O2CR2) CCH.