Chiral Iodoarenes and Iodanes for Transition Metal-free Asymmetric Reactions and Total Synthesis of Natural Products
Professor, SQuideau Lab
Institut des Sciences Moléculaires (CNRS-UMR 5255)
Université Bordeaux, France
Wednesday, April 24, 2019
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. 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.
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. 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] 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]
 Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
 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.
 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.
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