616227-06-6Relevant academic research and scientific papers
Design of chiral boronate-substituted acrylanilides. Self-activation and boron-transmitted 1,8-stereoinduction in [4+2] cycloaddition
Kennedy, Jason W.J.,Hall, Dennis G.
, p. 263 - 270 (2007/10/03)
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 show that dialkoxyboronic esters can operate as weak, internal Lewis acids and activate carbonyl-containing functionalities in cycloaddition reactions.
Self-activation and 1,8-stereoinduction in a boronate-substituted dienophile
Kennedy, Jason W. J.,Hall, Dennis G.
, p. 477 - 479 (2007/10/03)
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 and 10 provided a small level of remote 1,8-stereoinduction. These results show that dialkoxyboronic esters can operate as weak, internal Lewis acids and activate carbonyl-containing functionalities in cycloaddition reactions.
