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...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2020-08, Vol.85 (15), p.10175-10181
Main Authors: Pandey, Chandra Bhan, Azaz, Tazeen, Verma, Ram Subhawan, Mishra, Monika, Jat, Jawahar L, Tiwari, Bhoopendra
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00347