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Stereoselective [2+2]-Cycloadditions of chiral allenic ketones and alkenes: Applications towards the synthesis of benzocyclobutenes and endiandric acids

https://doi.org/10.1016/j.tet.2022.132932

Guo, Renyu ; Witherspoon, Brittany P. ; Brown, M. Kevin ( September 2022 , Tetrahedron)

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Evolution of a Strategy for the Enantioselective Synthesis of (−)-Cajanusine

https://doi.org/10.1021/jacs.0c00359

Guo, Renyu ; Witherspoon, Brittany P. ; Brown, M. Kevin ( March 2020 , Journal of the American Chemical Society)

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Stereoselective [4+2]‐Cycloaddition with Chiral Alkenylboranes

https://doi.org/10.1002/ange.202000652

Ni, Dongshun ; Witherspoon, Brittany P. ; Zhang, Hong ; Zhou, Chen ; Houk, K. N. ; Brown, M. Kevin ( May 2020 , Angewandte Chemie)

Abstract
A method for the stereoselective [4+2]‐cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N‐protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations of the C−B bond such as oxidation and homologation. Detailed computation evaluation of the reaction has uncovered a surprising role of the counterion on stereoselectivity.

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Stereoselective [4+2]‐Cycloaddition with Chiral Alkenylboranes

https://doi.org/10.1002/anie.202000652

Ni, Dongshun ; Witherspoon, Brittany P. ; Zhang, Hong ; Zhou, Chen ; Houk, K. N. ; Brown, M. Kevin ( May 2020 , Angewandte Chemie International Edition)

Abstract
A method for the stereoselective [4+2]‐cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N‐protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations of the C−B bond such as oxidation and homologation. Detailed computation evaluation of the reaction has uncovered a surprising role of the counterion on stereoselectivity.

more » « less