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 in | Journal of organic chemistry Vol. 85; no. 15; pp. 10175 - 10181 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
07.08.2020
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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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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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.0c00347 |