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Recent advances in asymmetric functionalization of olefins induced by chiral hypervalent iodine reagents

Wirth, Thomas and Zhang, Huaiyuan 2021. Recent advances in asymmetric functionalization of olefins induced by chiral hypervalent iodine reagents. Chinese Journal of Organic Chemistry 41 (1) , pp. 65-70. 10.6023/cjoc202006013

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Abstract

The functionalization of olefins induced by chiral hypervalent iodine reagents is a basic method for obtaining enantiomerically enriched chiral molecules and biologically active natural products. It is one of the new and promising fields in asymmetric synthesis. Throughout the past 20 years development in this area, on the one hand, stereoselective functionalizations of alkenes such as disulfonyloxylation, diacetoxylation, dihalogenation, diamination, hydroxylation-sulfonyloxylation and halogenation-alkylation and carbonylation have been successfully achieved with chiral hypervalent iodine reagents through intermolecular reactions, in which various functionalized products were enantioselectively obtained. On the other hand, many of hetero-cyclic compounds such as γ-butyrolactones, chromans, isochromans, oxazolidinones, piperidines, pyrrolidines and aziridines can be synthesized by intramolecular oxidative lactonization, etherification, amidation, arylation and other reactions, in which hypervalent iodine reagents can provide efficient methods for the synthesis of chiral heterocyclic compounds. In addition, various functionalization reactions of olefins mediated by chiral hypervalent iodine reagents can afford target compounds with excellent yield and enantioselectivity. Thus, this methodology has also been used in the total synthesis of natural products. The functionalization of olefins induced by chiral hypervalent iodine reagents and their applications in the total synthesis of natural products are reviewed.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Shanghai Institute of Organic Chemistry (SIOC)
ISSN: 0253-2786
Date of First Compliant Deposit: 2 September 2021
Date of Acceptance: 9 July 2020
Last Modified: 03 Sep 2021 15:00
URI: https://orca.cardiff.ac.uk/id/eprint/143853

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