• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

铑（I）催化2-亚烷基环丁醇与环状烯酮通过C-C键断裂进行的不对称[4 + 2]环加成反应：高效合成双环化合物。

Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C-C bond cleavage: efficient access to -bicyclic compounds.

作者信息

Zheng Xinxin, Guo Rui, Zhang Guozhu, Zhang Dayong

机构信息

Institute of Pharmaceutical Science , China Pharmaceutical University , Nanjing , P. R. China . Email:

State Key Laboratory of Organometallic Chemistry , Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , P. R. China . Email:

出版信息

Chem Sci. 2018 Jan 8;9(7):1873-1877. doi: 10.1039/c7sc04784c. eCollection 2018 Feb 21.

DOI:10.1039/c7sc04784c
PMID:29675233
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5890795/
Abstract

We report a rhodium-catalyzed asymmetric formal intermolecular [4 + 2] cycloaddition reaction of 2-alkylenecyclobutanols with α,β-unsaturated cyclic ketones leading to synthetically useful -bicyclic molecules. Three consecutive stereogenic centers are formed in a highly enantio- and diastereoselective manner. Stepwise C-C bond cleavage and annulation are likely involved in the reaction pathway. Here, iPr-Duphos is the viable chiral ligand that promotes excellent enantio-control.

摘要

我们报道了铑催化的2-亚烷基环丁醇与α,β-不饱和环酮的不对称形式分子间[4 + 2]环加成反应，该反应生成了具有合成价值的双环分子。三个连续的立体中心以高度对映和非对映选择性的方式形成。反应途径可能涉及逐步的C-C键断裂和环化。在此，异丙基-双膦配体是促进优异对映体控制的可行手性配体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/1a642d7e594b/c7sc04784c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/d853b20adf5c/c7sc04784c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/6b9d990f49e5/c7sc04784c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/8b1e243ff849/c7sc04784c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/1a642d7e594b/c7sc04784c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/d853b20adf5c/c7sc04784c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/6b9d990f49e5/c7sc04784c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/8b1e243ff849/c7sc04784c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abed/5890795/1a642d7e594b/c7sc04784c-s2.jpg

相似文献

1
Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C-C bond cleavage: efficient access to -bicyclic compounds.铑（I）催化2-亚烷基环丁醇与环状烯酮通过C-C键断裂进行的不对称[4 + 2]环加成反应：高效合成双环化合物。
Chem Sci. 2018 Jan 8;9(7):1873-1877. doi: 10.1039/c7sc04784c. eCollection 2018 Feb 21.
2
Organocatalyzed Enantio- and Diastereoselective Formal Domino 1,3-Dipolar Cycloaddition/Rearrangement: Synthesis of Chiral Pyrrolo-thiazine-2-carbaldehydes.有机催化的对映选择性和非对映选择性形式多米诺1,3-偶极环加成/重排反应：手性吡咯并噻嗪-2-甲醛的合成
Org Lett. 2024 Apr 19;26(15):2971-2975. doi: 10.1021/acs.orglett.4c00544. Epub 2024 Mar 28.
3
Enantio-, Diastereo- and Regioselective Synthesis of Chiral Cyclic and Acyclic gem-Difluoromethylenes by Palladium-Catalyzed [4+2] Cycloaddition.钯催化[4+2]环加成反应实现手性环状和非环状偕二氟亚甲基的对映选择性、非对映选择性和区域选择性合成
Angew Chem Int Ed Engl. 2022 Jun 13;61(24):e202117635. doi: 10.1002/anie.202117635. Epub 2022 Apr 13.
4
BINOL Phosphoric Acid-Catalyzed Asymmetric Mannich Reaction of Cyclic N-Acyl Ketimines with Cyclic Enones.联萘酚磷酸催化环状N-酰基酮亚胺与环状烯酮的不对称曼尼希反应
Chem Asian J. 2019 Sep 2;14(17):2958-2965. doi: 10.1002/asia.201900556. Epub 2019 Aug 7.
5
Oxidative Asymmetric Formal Aza-Diels⁻Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones.四氢-β-咔啉与烯酮的不对称氧化环加成反应在吲哚喹啉-2-酮中的合成。
Molecules. 2018 Sep 1;23(9):2228. doi: 10.3390/molecules23092228.
6
Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.铑催化的3-酰氧基-1,4-烯炔与烯烃的立体选择性分子内[5+2]环加成反应
Org Lett. 2015 Oct 16;17(20):5128-31. doi: 10.1021/acs.orglett.5b02665. Epub 2015 Oct 6.
7
Enantioselective Carbonyl 1,2- or 1,4-Addition Reactions of Nucleophilic Silyl and Diazo Compounds Catalyzed by the Chiral Oxazaborolidinium Ion.手性噁唑硼烷离子催化的亲核硅基和重氮化合物的羰基 1,2-或 1,4-加成反应。
Acc Chem Res. 2019 Aug 20;52(8):2349-2360. doi: 10.1021/acs.accounts.9b00279. Epub 2019 Jul 17.
8
Asymmetric [3 + 2] Cycloaddition Employing N, N'-Cyclic Azomethine Imines Catalyzed by Chiral-at-Metal Rhodium Complex.手性金属铑配合物催化的 N，N′-环亚胺亚甲腙不对称 [3 + 2] 环加成反应。
Org Lett. 2018 Jun 1;20(11):3354-3357. doi: 10.1021/acs.orglett.8b01264. Epub 2018 May 15.
9
Rhodium-Catalyzed Dynamic Kinetic [4+2] Cycloaddition of Allene-1,3-Dienes.铑催化的丙二烯-1,3-二烯的动态动力学[4+2]环加成反应。
Angew Chem Int Ed Engl. 2022 Nov 21;61(47):e202211635. doi: 10.1002/anie.202211635. Epub 2022 Oct 21.
10
Highly Enantio- and s-trans C=C bond selective catalytic hydrogenation of cyclic enones: alternative synthesis of (-)-menthol.环状烯酮的高对映体选择性和s-反式C=C键选择性催化氢化反应：（-）-薄荷醇的另一种合成方法
Chemistry. 2008;14(7):2060-6. doi: 10.1002/chem.200701505.

引用本文的文献

1
Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.手性钌催化苯并环丁烯酮-酮醇环加成反应：结合 C-C 键活化和转移氢化偶联构建 II 型聚酮。
J Am Chem Soc. 2018 Jul 25;140(29):9091-9094. doi: 10.1021/jacs.8b05724. Epub 2018 Jul 11.

本文引用的文献

1
Direct activation of relatively unstrained carbon-carbon bonds in homogeneous systems.均相体系中相对无张力碳-碳键的直接活化
Org Chem Front. 2014 Jul 1;1(5):567-581. doi: 10.1039/c4qo00053f. Epub 2014 Mar 27.
2
Divergent reactivities in fluoronation of allylic alcohols: synthesis of -fluoroalkenes carbon-carbon bond cleavage.烯丙醇氟化反应中的不同反应性：-氟代烯烃的合成与碳-碳键断裂
Chem Sci. 2017 May 1;8(5):3885-3890. doi: 10.1039/c7sc00483d. Epub 2017 Mar 20.
3
Development of Batch and Flow Immobilized Catalytic Systems with High Catalytic Activity and Reusability.
具有高催化活性和可重复使用性的间歇式和流动式固定化催化体系的开发。
Chem Pharm Bull (Tokyo). 2017;65(9):805-821. doi: 10.1248/cpb.c17-00349.
4
Expedient Synthesis of 1,5-Diketones by Rhodium-Catalyzed Hydroacylation Enabled by C-C Bond Cleavage.通过 C-C 键断裂实现铑催化氢酰化的 1,5-二酮的便捷合成。
J Am Chem Soc. 2017 Sep 20;139(37):12891-12894. doi: 10.1021/jacs.7b05427. Epub 2017 Sep 7.
5
Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp)-C(sp) bond cleavage.铑（I）催化氧杂环丁醇与炔烃通过C（sp）-C（sp）键裂解进行的立体选择性[4+2]环加成反应。
Chem Sci. 2017 Apr 1;8(4):3002-3006. doi: 10.1039/c6sc05246k. Epub 2017 Jan 23.
6
Z-Selective Synthesis of γ,δ-Unsaturated Ketones via Pd-Catalyzed Ring Opening of 2-Alkylenecyclobutanones with Arylboronic Acids.钯催化 2-烯丙基环丁酮与芳基硼酸的开环反应实现 Z-选择性合成 γ,δ-不饱和酮
Org Lett. 2016 Aug 19;18(16):4000-3. doi: 10.1021/acs.orglett.6b01816. Epub 2016 Aug 1.
7
Microbial diversification of Diels-Alder cycloadducts by whole cells of Penicillium brasilianum.巴西青霉全细胞对狄尔斯-阿尔德环加成物的微生物多样性作用
Mol Divers. 2016 Nov;20(4):877-885. doi: 10.1007/s11030-016-9680-0. Epub 2016 Jun 1.
8
Some chemical speculation on the biosynthesis of corallidictyals A-D.关于珊瑚盘菌素A-D生物合成的一些化学推测。
Org Biomol Chem. 2016 Jun 28;14(24):5546-9. doi: 10.1039/c6ob00171h. Epub 2016 Feb 22.
9
C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives.锰催化氧化开环氰化和炔基化环丁醇衍生物的 C-C 键形成策略。
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2866-9. doi: 10.1002/anie.201510973. Epub 2016 Jan 22.
10
Rh(I)-Catalyzed Insertion of Allenes into C-C Bonds of Benzocyclobutenols.铑（I）催化的丙二烯对苯并环丁烯醇 C-C 键的插入反应。
Org Lett. 2016 Jan 15;18(2):328-31. doi: 10.1021/acs.orglett.5b03518. Epub 2016 Jan 4.