- Activation of the hypervalent fluoroiodane reagent by hydrogen bonding to hexafluoroisopropanol
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Hexafluoroisopropan-2-ol (HFIP) is an excellent solvent for promoting fluorinations with the hypervalent fluoroiodane reagent 1 and crucially, it removes the need for transition metals or TREAT-HF activators. The fluoroiodane reagent 1 was used in HFIP to monofluorinate 1,3-ketoesters and to fluorocyclise unsaturated carboxylic acids in excellent yields under mild reaction conditions.
- Minhas, Harsimran K.,Riley, William,Stuart, Alison M.,Urbonaite, Martyna
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supporting information
p. 7170 - 7173
(2018/10/24)
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- Ru-catalyzed asymmetric hydrogenation of δ-keto Weinreb amides: Enantioselective synthesis of (+)-Centrolobine
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An efficient asymmetric hydrogenation of δ-keto Weinreb amides catalyzed by a Ru-Xyl-SunPhos-Daipen bifunctional catalyst has been achieved. This method afforded a series of enantio-enriched δ-hydroxy Weinreb amides in good yields (up to 93%) and enantioselectivities (up to 99%). This protocol was successfully applied to the synthesis of the key intermediate of (+)-Centrolobine.
- Zhao, Mengmeng,Lu, Bin,Ding, Guangni,Ren, Kai,Xie, Xiaomin,Zhang, Zhaoguo
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p. 2723 - 2730
(2016/03/05)
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- Intramolecular fluorocyclizations of unsaturated carboxylic acids with a stable hypervalent fluoroiodane reagent
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A new class of fluorinated lactones was prepared by the intramolecular fluorocyclizations of unsaturated carboxylic acids by using the stable fluoroiodane reagent in combination with AgBF4. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step. The fluoroiodane reagent, prepared easily from fluoride, can also be used without a metal catalyst to give moderate yields within just 1 hour, thus demonstrating that it is a suitable reagent for developing new 18F-labelled radiotracers for PET imaging. All in one: A new class of lactones containing a tertiary alkyl fluoride was prepared in high yields by using a stable fluoroiodane reagent. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step.
- Geary, Gemma C.,Hope, Eric G.,Stuart, Alison M.
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supporting information
p. 14911 - 14914
(2016/02/05)
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- Enantioselective synthesis of Indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl Isocyanates and terminal alkynes
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An enantioselective synthesis of Indolizidines bearing quaternary substituted stereocenters by way of a rhodium-catalyzed [2 + 2 + 2] cycloaddition of substituted alkenyl Isocyanates and terminal alkynes Is described. The reaction provides lactam products using aliphatic alkynes, whereas aryl alkynes give rise to vlnylogous amide products. Through modification of the phosphoramldlte llgand, high levels of enantloselectlvlty, regloselectlvlty, and product selectivity are obtained for both products.
- Lee, Ernest E.,Rovis, Tomislav
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supporting information; body text
p. 1231 - 1234
(2009/04/07)
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