Design of chiral boronate-substituted acrylanilides.: Self-activation and boron-transmitted 1, 8-stereoinduction in [4+ 2] cycloaddition

JWJ Kennedy, DG Hall

Index: Kennedy, Jason W.J.; Hall, Dennis G. Journal of Organometallic Chemistry, 2003 , vol. 680, # 1-2 p. 263 - 270

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Citation Number: 3

Abstract

The [4+ 2] cycloaddition of ortho-boronoanilide dienophile 4 with cyclopentadiene was found to proceed faster than both its para isomer 8 and the unsubstituted derivative 6, thereby confirming that self-activation by internal coordination is operative in the case of 4. Chiral boronic esters derivatives 9–13 provided a small level of remote 1, 8-stereoinduction transmitted through a putative tetrahedral stereogenic boronate complex. These results ...