A Chiral Pentafluorinated Isopropyl Group via Iodine(I)/(III) Catalysis
An I(I)/(III) catalysis strategy to construct an enantioenriched fluorinated isostere of the iPr group is reported. The difluorination of readily accessible α-CF3-styrenes is enabled by the in situ generation of a chiral ArIF2 species to forge a stereocentre with the substituents F, CH2F and CF3 (up to 95 %, >20:1 vicinal:geminal difluorination). The replacement of the metabolically labile benzylic proton results in a highly preorganised scaffold as was determined by X-ray crystallography (π→σ* and stereoelectronic gauche σ→σ* interactions). A process of catalyst editing is disclosed in which preliminary validation of enantioselectivity is placed on a structural foundation.
Meyer, Stephanie,H?fliger, Joel,Sch?fer, Michael,Molloy, John J.,Daniliuc, Constantin G.,Gilmour, Ryan
p. 6430 - 6434
(2021/02/26)
Enantioselective metal-free diamination of styrenes
Metal-free and asymmetric: The first enantioselective diamination of styrenes simply requires a chiral hypervalent iodine(III) reagent as an oxidant and bismesylimide as a nitrogen source (see scheme, Ms=methanesulfonyl). The reaction proceeds under mild conditions and with high enantiomeric excess.
Roeben, Caren,Souto, Jose A.,Gonzalez, Yolanda,Lishchynskyi, Anton,Muniz, Kilian
supporting information; experimental part
p. 9478 - 9482
(2011/11/06)
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