Organoiodine-Catalyzed Enantioselective Alkoxylation/Oxidative Rearrangement of Allylic Alcohols

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2019 Apr 4

PMID 30942948

Citations 6

Authors

Dong-Yang Zhang

Ying Zhang

Hua Wu

Liu-Zhu Gong

Affiliations

Soon will be listed here.

Abstract

An enantioselective catalytic alkoxylation/oxidative rearrangement of allylic alcohols has been established by using a Brønsted acid and chiral organoiodine. The presence of 20 mol % of an (S)-proline-derived C -symmetric chiral iodine led to enantioenriched α-arylated β-alkoxylated ketones in good yields and with high levels of enantioselectivity (84-94 % ee).

Citing Articles

Enantioselective Synthesis of α-Aryl Ketones by a Cobalt-Catalyzed Semipinacol Rearrangement.

Kalomenopoulos P, Emayavaramban B, Johnston C Angew Chem Int Ed Engl. 2024; 64(2):e202414342.

PMID: 39312676 PMC: 11720393. DOI: 10.1002/anie.202414342.

Chemoselective cycloisomerization of O-alkenylbenzamides via concomitant 1,2-aryl migration/elimination mediated by hypervalent iodine reagents.

He J, Du F, Zhang C, Du Y Commun Chem. 2023; 6(1):126.

PMID: 37330613 PMC: 10276869. DOI: 10.1038/s42004-023-00930-5.

Chiral Iodotriptycenes: Synthesis and Catalytic Applications.

Khan N, Itaya K, Wirth T ChemistryOpen. 2022; 11(7):e202200145.

PMID: 35822927 PMC: 9278095. DOI: 10.1002/open.202200145.

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides.

Bartolo N, Demkiw K, Read J, Valentin E, Yang Y, Dillon A J Org Chem. 2022; 87(5):3042-3065.

PMID: 35167300 PMC: 9022492. DOI: 10.1021/acs.joc.1c02844.

Recent development and applications of semipinacol rearrangement reactions.

Zhang X, Li B, Wang S, Zhang K, Zhang F, Tu Y Chem Sci. 2021; 12(27):9262-9274.

PMID: 34349896 PMC: 8314203. DOI: 10.1039/d1sc02386a.