Stereoselective Oxidative Rearrangement of Disubstituted Unactivated Alkenes Using Hypervalent Iodine(III) Reagent

The stereoselective oxidative rearrangement of disubstituted unactivated olefins has been achieved using a hypervalent iodine­(III) reagent. The aryl group undergoes 1,2-migration to give tert-α-arylated aldehydes (as acetals). The preparation of these aldehydes/acetals, especially containing a tert...

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Published inJournal of organic chemistry Vol. 85; no. 15; pp. 10175 - 10181
Main Authors Pandey, Chandra Bhan, Azaz, Tazeen, Verma, Ram Subhawan, Mishra, Monika, Jat, Jawahar L, Tiwari, Bhoopendra
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
N-H
OLEFINS
STEREOSPECIFIC SYNTHESIS
ALDEHYDES
METAL
ENANTIOSELECTIVE ALPHA-ARYLATION
AZIRIDINES
CATALYSTS
EPOXIDATION
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Summary:The stereoselective oxidative rearrangement of disubstituted unactivated olefins has been achieved using a hypervalent iodine­(III) reagent. The aryl group undergoes 1,2-migration to give tert-α-arylated aldehydes (as acetals). The preparation of these aldehydes/acetals, especially containing a tert-benzylic stereocenter, has remained challenging. This migration-based method provides a complementary approach over the known α-substitution-based methods for accessing this class of molecules.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00347