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化学进展 2021, Vol. 33 Issue (6): 895-906 DOI: 10.7536/PC200758   后一篇

• 综述 •

氧杂环丁烷的合成

符志成, 许家喜*()   

  1. 北京化工大学化学学院有机化学系 化工资源有效利用国家重点实验室 北京 100029
  • 收稿日期:2020-07-28 修回日期:2020-09-29 出版日期:2021-06-20 发布日期:2020-12-28
  • 通讯作者: 许家喜
  • 基金资助:
    国家自然科学(21572017); 国家自然科学(21772010)
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Synthesis of Oxetanes

Zhicheng Fu, Jiaxi Xu*()   

  1. State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China
  • Received:2020-07-28 Revised:2020-09-29 Online:2021-06-20 Published:2020-12-28
  • Contact: Jiaxi Xu
  • About author:
    * Corresponding author e-mail:
  • Supported by:
    National Natural Science Foundation of China(21572017); National Natural Science Foundation of China(21772010)

氧杂环丁烷作为一类饱和四元环醚类化合物,不仅是重要的有机合成中间体,也是天然和合成的具有抗癌、抗HIV、抑制谷氨酰胺合成酶等多种生物或药物活性化合物分子结构中的重要活性单元。因此,发展氧杂环丁烷骨架的有效合成方法非常重要。本文以分子内形成C—C键的环化反应、分子内形成C—O键的Williamson醚化反应、烯烃和醛酮[2+2]光环加成反应(Paternò-Büchi反应)、过渡金属催化的形式[2+2]环加成反应、硫叶立德介导的环氧乙烷扩环反应和C—H键氧化环化反应等方面较系统综述了近5年内关于氧杂环丁烷合成方法的新进展。希望本文能为致力于发展构建氧杂环丁烷骨架的有机合成化学家提供一些有价值的信息,以便促进氧杂环丁烷合成方法的发展及应用。

关键词： 氧杂环丁烷, 扩环, 环化, 环加成, C—H氧化环化

Oxetanes are a class of saturated four-membered cyclic ether compounds. They are not only an important class of organic synthetic intermediates, but also crucial active structural units of natural and synthetic biological and medicinal active compounds possessing anti-cancer, inhibition of human immunodeficiency virus, as well as inhibiting glutamine synthetase in clinical practice. Thus, it is in high demand to develop efficient methods for constructing oxetane structural motifs. In this review, the intramolecular cyclization reaction via C—C bond formation, the intramolecular Williamson etherification by the formation of C—O bond, the [2+2] photocycloadditions of alkenes with aldehydes and ketones(named as Paternò-Büchi reaction), transition metal catalyzed formal [2+2] cycloadditions, sulfide ylide-mediated epoxide ring expansion, and the C—H bond oxidative cyclization are reviewed with a focus on new progress in the synthesis of oxetanes during the last five years. It is hoped that this review can provide some valuable information for the organic chemists who are interested in the construction of the oxetane skeleton and promote the development on the synthesis and application of oxetanes.

Contents

1 Introduction

2 Cyclization through the C—C bond formation

3 Cyclization through the C—O bond formation

4 Ring expansion reaction of epoxides

5 [2+2] Cycloadditions

5.1 Paternò-Büchi [2+2] photocycloadditions

5.2 Formal [2+2] cycloadditions

6 C—H bond oxidative cyclizations

7 Conclusion

Key words: oxetane, ring expansion, cyclization, cycloaddtion, C—H oxidative cyclization
()
图1 含氧杂环丁烷结构的天然产物和合成药物[23⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓~40]
Fig.1 Natural products and synthetic bioactive compounds containing the oxetane motif[23⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓~40]
图式1 通过C—C键形成合成2-磺酰基氧杂环丁烷化合物[51]
Scheme 1 Synthesis of 2-sulfonyloxetanes via the C—C bond formation[51]
图式2 铑催化C—C键环化构建多取代氧杂环丁烷化合物[52]
Scheme 2 Rhodium-catalyzed C—C cyclization access to multisubstituted oxetane derivatives[52]
图式3 通过卡宾插入反应形成C—C键合成3-位螺环氧杂环丁烷产物15a~15g[53]
Scheme 3 Synthesis of 3-spiro-oxetanes 15a~15g through the C—C bond formation by the C—H carbene insertion[53]
图式4 Williamson 醚化合成氧杂环丁烷[54]
Scheme 4 Williamson etherification to oxetanes[54]
图式5 C—O键形成分子内环化反应的常见方法[55⇓⇓⇓⇓~60]
Scheme 5 Common methods of cyclization through the C—O bond formation[55⇓⇓⇓⇓~60]
图式6 硒砜介导的加成及环化反应合成螺吲哚啉酮-氧杂环丁烷化合物[61]
Scheme 6 Selenone-mediated cyclizations to spirooxindolinone-oxetanes[61]
图式7 金催化炔丙醇合成氧杂环丁烷酮[62]
Scheme 7 Gold-catalyzed synthesis of oxetan-2-ones from readily available propargylic alcohols[62]
图式8 铱催化含全碳取代季碳立体中心的氧杂环丁烷的对映选择性合成[63]
Scheme 8 Iridium-catalyzed enantioselective synthesis of oxetanes bearing an all-carbon substituted quaternary stereocenter[63]
图式9 抗精神病药物Haloperidol类似物的合成[63]
Scheme 9 Synthesis of an oxetane-bearing analogue of the antipsychotic agent Haloperidol[63]
图式10 硫叶立德和氧杂环丙烷的扩环反应[76]
Scheme 10 Ring expansion of dimethyloxosulfonium methylide and epoxides[76]
图式11 通过Corey-Chaykovsky环氧化和扩环反应合成2-三氟甲基氧杂环丁烷[82]
Scheme 11 Synthesis of 2-trifluoromethyloxetanes via the Corey-Chaykovsky epoxidation and ring expansion[82].
图式12 含2-三氟甲基氧杂环丁烷的γ-分泌酶调节剂类似物45的合成[82]
Scheme 12 Synthesis of γ-secretase modulator analogue 45 containing 2-trifluorooxetane [82]
图式13 第一例Paternò-Büchi 反应[2⇓~4]
Scheme 13 The first Paternò-Büchi reaction[2⇓~4]
图式14 Paternò-Büchi 反应的主要机理[83]
Scheme 14 Main mechanism of the Paternò-Büchi reaction[83]
图式15 光促进的累积二烯与酮合成2-亚烷基氧杂环丁烷[84]
Scheme 15 Light-promoted synthesis of 2-alkylideneoxetanes from allenoates and ketones[84]
图式16 铜(Ⅰ)催化酮羰基化合物与烯烃分子间[2+2]环加成反应[85]
Scheme 16 Cu(Ⅰ)-catalyzed intermolecular [2 + 2] photocycloadditions of carbonyl compounds and norbornene[85]
图2 光活性物种TpCu-(Norb) 54[85]
Fig.2 Photoactive species TpCu-(Norb) 54[85]
图式17 羰基与降冰片烯分子间[2+2]光环加成反应机理[85]
Scheme 17 Mechanism of intermolecular [2 + 2] photocycloadditions of carbonyl compounds and norbornene[85]
图式18 可见光促进烯烃与羰基的[2+2]环加成反应[86]
Scheme 18 Visible-light promoted [2 + 2] cycloaddition of alkenes and carbonyls[86]
图式19 过渡金属催化的形式[2+2]环加成反应[87,88]
Scheme 19 Transition metal-catalyzed formal [2+2] cycloadditions[87,88]
图式20 DABCO催化的形式[2+2]环加成反应[89]
Scheme 20 DABCO-catalyzed formal [2+2] cycloaddition[89]
图式21 DABCO催化的形式[2+2]环加成反应的机理[89]
Scheme 21 Mechanism of DABCO-catalyzed formal [2+2] cycloaddition[89]
图式22 β-ICD 催化的丙二烯酸酯与酮不对称形式[2+2]环加成反应[90]
Scheme 22 β-ICD-catalyzed asymmetric formal [2+2] cycloaddition of allenoates with ketones[90]
图式23 NHC催化形式[2+2]环加成反应[93]
Scheme 23 NHC-catalyzed formal [2+2] annulations of allenoates[93]
图式24 氧杂环丁烷的衍生化反应[93]
Scheme 24 Derivatization of oxetane products[93]
图式25 NHC催化形式[2+2]环加成反应的反应机理[93]
Scheme 25 Proposed catalytic cycle for NHC-catalyzed formal [2+2] annulation[93]
图3 (-)-Mitrephorone A 的结构[94]
Fig.3 Structure of(-)-Mitrephorone A[94]
图式26 C—H键氧化环化实现天然产物(-)-Mitrephorone A的不对称全合成[95]
Scheme 26 Total synthesis of (-)-mitrephorone A via C—H oxidative cyclization[95]
图式27 由(-)-Mitrephorone B中C—H键氧化环化合成(-)-Mitrephorone A[96]
Scheme 27 Synthesis of(-)-Mitrephorone A via a bio-inspired late stage C—H oxidative cyclization of(-)-Mitrephorone B[96]
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摘要

氧杂环丁烷的合成