Chemistry Seminar Series: Laurent Pouységu

Wednesday, April 24, 2019 2:00 pm - 2:00 pm EDT

Chiral Iodoarenes and Iodanes for Transition Metal-free Asymmetric Reactions and Total Synthesis of Natural Products

Laurent Pouységu
Professor, SQuideau Lab
Institut des Sciences Moléculaires (CNRS-UMR 5255)
Université Bordeaux, France

Wednesday,  April 24, 2019
2:00 p.m.
C2-361 (Reading Room)


       Over the last decade, the search for chiral iodoarenes and iodanes has been one of the most competitive area of investigations in hypervalent iodine chemistry, as these reagents represent a promising alternative to the use of (gradually rarefying) transition metals.[1] A wide number of chiral iodoarenes and iodanes have thus been described worldwide, and their evaluation in stereoselective (organoiodo-catalytic) transformations has led to a short list of truly efficient systems.[1]

       In this context, our research team has been developing its own chiral iodocompounds based on structurally diverse biarylic (e.g., A and D), Salen-type (e.g., B and C) and helicenic (e.g., E) scaffolds.[2] These chiral reagents have mostly been successfully applied in asymmetric (and biomimetic) C–O bond-forming transition metal-free methodologies [e.g., the hydroxylative phenol dearomatization (HPD) reaction][3] and illustrated by the total synthesis of natural products, such as bisthymol, scyphostatin analogues, bacchopetiolone and maytenone.[2a-d,f] More recently, these chiral iodoarenes/iodanes have been investigated in more challenging stereoselective C–C bond-forming events.[2e]

Selection of Chiral iodaarenes and iodanes developed by our team and Natural products synthesized through iodane-mediated methods.

[1] Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.

[2] Quideau, S.; Pouységu, L. et al.: a) Angew. Chem. Int. Ed. 2009, 48, 4605; b) Angew. Chem. Int. Ed. 2014, 53, 9860; c) Org. Lett. 2016, 18, 1120; d) J. Org. Chem. 2017, 82, 11816; e) Chem. Eur. J. 2017, 23, 2852; f) Chem. Eur. J. 2019, 25, 2852.

[3] Quideau, S.; Pouységu, L.; Peixoto, P. A.; Deffieux, D. In Topics Curr. Chem. 2016, Vol. 373 (In Hypervalent Iodine Chemistry; Ed.: T. Wirth), pp. 25-74; Springer.