Synthesis of spirocyclic scaffolds using hypervalent iodine reagents
نویسندگان
چکیده
منابع مشابه
Asymmetric Synthesis with Hypervalent Iodine Reagents.
This chapter describes recent developments in stereoselective synthesis using hypervalent iodine reagents.
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We present a review of natural product syntheses accomplished in our laboratory during the last 5 years. Each synthetic route features a phenol dearomatization promoted by an environmentally benign hypervalent iodine reagent. The dearomatizations demonstrate the "aromatic ring umpolung" concept, and involve stereoselective remodeling of the inert unsaturations of a phenol into a highly function...
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Aromatic substituents migrate in a novel oxidative cyclization mediated by iodine(III) reagents. 4-Arylbut-3-enoic acids are cyclized and rearranged to 4-arylfuran-2(5H)-ones by hypervalent iodine compounds in good to excellent yields under mild reaction conditions. Other ring sizes are also accessible. The mechanism of the reaction is described in detail, and calculations highlight the cationi...
متن کاملThioamination of Alkenes with Hypervalent Iodine Reagents
An efficient thioamination of alkenes mediated by iodine(III) reagents is described. The use of different sulfur nucleophiles allows the flexible synthesis of 1,2-aminothiols from alkenes. By employing chiral iodine(III) reagents, a stereoselective version of the thioamination protocol has also been developed.
متن کاملStereoselective Ketone Rearrangements with Hypervalent Iodine Reagents.
The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.
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ژورنال
عنوان ژورنال: Beilstein Journal of Organic Chemistry
سال: 2018
ISSN: 1860-5397
DOI: 10.3762/bjoc.14.152