Recent Advances in Asymmetric Functionalization of Olefins Induced by Chiral Hypervalent Iodine Reagents

doi:10.6023/cjoc202006013

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.

Key words: Keywords chiral hypervalent iodine reagents, olefins, functionalization, asymmetric synthesis

Cite this article

Huaiyuan Zhang, Thomas Wirth. Recent Advances in Asymmetric Functionalization of Olefins Induced by Chiral Hypervalent Iodine Reagents[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 65-70.

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Fig. & Tab. 18

Scheme 1. Asymmetric Prévost and Woodward reactions induced by chiral hypervalent iodine compound 15 or 16

Scheme 2. Mechanism of asymmetric double amidation of olefins 5 induced by chiral hypervalent iodine compound 21

Scheme 3. Mechanism of asymmetric rearrangement of olefins 30 induced by chiral hypervalent iodine compound 21

Scheme 4. Reaction and mechanism of asymmetric rearrangement of olefins 42 induced by chiral aryl iodide 43

Scheme 5. Mechanism of oxidative hydrolysis of haloalkene 51 induced by chiral aryl iodide 52

Scheme 6. Asymmetric fluorination-cyclization of alkene 64 induced by chiral aryl iodide 62

Scheme 7. The mechanism of asymmetric difluorination of alkenes 73 induced by chiral aryl iodide 68

Scheme 8. Mechanism of the asymmetric double amidation of alkenes 5 induced by chiral aryl iodide 77

Scheme 9. Asymmetric lactonization of alkene 83 induced by chiral hypervalent iodine compound 84

Scheme 10. Asymmetric tetrahydrofuranylation of alkenes 88 induced by chiral hypervalent iodine compound 15 or 89

Scheme 11. Asymmetric oxylactonization of alkenes 93 induced by chiral hypervalent iodine compound 15, 16 or 21

Scheme 12. Asymmetric amination-cyclization of alkene 97 induced by chiral hypervalent iodine compound 98

Scheme 13. Mechanism of asymmetric arylation of alkenes 120 induced by chiral hypervalent iodine compound 15, 21 or 89

Scheme 14. The asymmetric oxidative arylation of alkenes 126 induced by chiral hypervalent iodine compound 15 or127

Scheme 15. Mechanism of asymmetric fluorination-amination of alkenes 132 induced by chiral aryl iodide 68

Scheme 16. Total synthesis of the natural product 145

Scheme 17. Total synthesis of (12S)- and (12R)-Hydroxymonocerins

Scheme 18. Synthesis of (3R,4R)-4-Hydroxymellein 156a and (3R,4R)-4-Hydroxy-6-methoxymellein 156b

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手性高价碘试剂诱导的烯烃不对称官能团化反应研究进展