Dirhodium carboxylate catalysts from 2-fenchyloxy or 2-menthyloxy arylacetic acids: enantioselective C-H insertion, aromatic addition and oxonium ylide formation/rearrangement

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Date
2021-10
Authors
Buckley, Aoife
Crowley, Daniel C.
Brouder, Thomas A.
Ford, Alan
Khandavilli, Udaya Bhaskara Rao
Lawrence, Simon E.
Maguire, Anita R.
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WILEY-VCH Verlag
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Abstract
A new class of dirhodium carboxylate catalysts have been designed and synthesized from 2-fenchyloxy or 2-menthyloxy arylacetic acids which display excellent enantioselectivity across a range of transformations of alpha-diazocarbonyl compounds. The catalysts were successfully applied to enantioselective C-H insertion reactions of aryldiazoacetates and alpha-diazo-beta-oxosulfones affording the respective products in up to 93 % ee with excellent trans diastereoselectivity in most cases. Furthermore, efficient desymmetrization in an intramolecular C-H insertion was achieved. In addition, these catalysts prove highly enantioselective for intramolecular aromatic addition with up to 88% ee, and oxonium ylide formation and rearrangement with up to 74% ee.
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Intramolecular buchner reaction , Sigmatropic rearrangement , Asymmetric-synthesis , Carbene insertion , HIV-1 integrase , Complexes , Bond , Functionalization , Diazoketones , Derivatives
Citation
Buckley, A. M., Crowley D. C., Brouder; T. A., Ford, A; Khandavilli, U. B. R., Lawrence, S. E. and Maguire, A. R. (2021) 'Dirhodium carboxylate catalysts from 2-fenchyloxy or 2-menthyloxy arylacetic acids: enantioselective C-H insertion, aromatic addition and oxonium ylide formation/rearrangement', ChemCatChem, 13 , pp. 4318-4324. doi:10.1002/cctc.202100924