Electrochemical Semipinacol Rearrangements of Allylic Alcohols: Construction of All-Carbon Quaternary Stereocenters

Electrochemical Semipinacol Rearrangements of Allylic Alcohols: Construction of All-Carbon Quaternary Stereocenters

The first examples of electrochemical trifluoromethylation and sulfonylation/semipinacol rearrangements of allylic alcohols were developed using cheap and stable RSO2Na (R = CF3, Ph) as reagents. Various β-trifluoromethyl and sulfonated ketones were obtained in moderate to excellent yields. This str...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters Vol. 21; no. 8; pp. 2536 - 2540
Main Authors: Kang, Jun-Chen, Tu, Yong-Qiang, Dong, Jia-Wei, Chen, Chao, Zhou, Jia, Ding, Tong-Mei, Zai, Jian-Tao, Chen, Zhi-Min, Zhang, Shu-Yu
Format: Journal Article
Language:English
Published: United States American Chemical Society 19-04-2019
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The first examples of electrochemical trifluoromethylation and sulfonylation/semipinacol rearrangements of allylic alcohols were developed using cheap and stable RSO2Na (R = CF3, Ph) as reagents. Various β-trifluoromethyl and sulfonated ketones were obtained in moderate to excellent yields. This strategy provides a facile, direct, and complementary approach to construct all-carbon quaternary stereocenters. In addition, the reaction has the advantages of being chemical oxidant-free and metal-free and has safe and mild reaction conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00263