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

doi:10.6023/cjoc202006013

摘要/Abstract

手性高价碘试剂诱导的烯烃官能团化是获得对映体富集的手性分子和具有生物活性天然产物的基本方法, 是不对称合成中一个崭新且富有成效的领域之一. 纵观20年来该领域的发展, 在手性高价碘诱导下, 一方面通过分子间的官能团化实现了双键的双磺酰氧基化、双乙酰氧基化、双卤化、双胺化、羟基化-磺酰氧基化、卤化-烷基化及羰基化等, 对映选择性地合成了各种官能团化的产物; 另一方面通过分子内的氧化内酯化、醚化、酰胺化、芳基化等反应, 对映选择性地合成了 γ-丁内酯、色满环、异色满环、噁唑烷酮、哌啶、吡咯烷、氮杂环丙烷等各种环状化合物, 为手性杂环化合物的合成提供了有效途径. 此外, 由于手性高价碘高效诱导烯烃发生各种官能团化, 提供了优秀的产率和对映选择性, 因此, 该方法学已被用于天然产物的全合成中. 就近二十年来手性高价碘试剂诱导的烯烃官能团化及其在天然产物全合成中的应用进行综述.

关键词: 手性高价碘试剂, 烯烃, 官能团化, 不对称合成

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

引用此文

张怀远, Thomas Wirth. 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[J]. 有机化学, 2021, 41(1): 65-70.

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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图/表 18

图式1. 手性高价碘化合物15或16诱导的不对称Prévost和Woodward反应

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

图式2. 手性高价碘化合物21诱导的烯烃5的不对称双酰胺化反应机理

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

图式3. 手性高价碘化合物21诱导的烯烃30的不对称重排反应机理

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

图式4. 手性芳基碘合物43诱导的烯烃42的不对称重排反应及机理

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

图式5. 手性芳基碘化物52诱导的卤代烯烃51的氧化水解反应机理

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

图式6. 手性芳基碘化物62诱导的烯烃64的不对称氟化-环化反应

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

图式7. 手性芳基碘化物68诱导的烯烃73的不对称双氟化反应机理

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

图式8. 手性芳基碘化物77诱导的烯烃5的不对称双酰胺化反应机理

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

图式9. 手性高价碘化合物84诱导的烯烃83的不对称内酯化反应

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

图式10. 手性高价碘化合物15或89诱导的烯烃88的不对称四氢呋喃基化反应

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

图式11. 手性高价碘化合物15、16或21诱导的烯烃93的不对称氧化内酯化反应

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

图式12. 手性高价碘化合物98诱导的烯烃97的不对称环化-胺基化反应

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

图式13. 手性高价碘化合物15、21或89诱导的烯烃120的不对称芳基化反应机理

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

图式14. 手性高价碘化合物15或127诱导的烯烃126的不对称氧化芳基化反应

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

图式15. 手性芳基碘化物68诱导的烯烃132的不对称氟化-胺基化反应机理

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

图式16. 天然产物145的全合成

Scheme 16. Total synthesis of the natural product 145

图式17. (12S)和(12R)-Hydroxymonocerins的全合成

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

图式18. (3R,4R)-4-羟基蜂蜜曲菌素156a和(3R,4R)-4-羟基-6-甲氧基蜂蜜曲菌素156b的合成

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

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