Highly diastereoselective and enantioselective formal [4+1] ylide annulation for the synthesis of optically active dihydrofurans

被引:95
|
作者
Zheng, Jun-Cheng [1 ]
Zhu, Chun-Yin [1 ]
Sun, Xiu-Li [1 ]
Tang, Yong [1 ]
Dai, Li-Xin [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 17期
基金
中国国家自然科学基金;
关键词
D O I
10.1021/jo801135j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
On the basis of the reactions of camphor-derived sulfur ylide with alpha-ylidene-beta-diketones, highly efficient and selective synthesis of optically active dihydrofurans has been achieved.
引用
收藏
页码:6909 / 6912
页数:4
相关论文
共 50 条
  • [21] Rhodium(II)-Catalyzed Formal [4+1]-Cycloaddition of Pyridotriazoles and Propargyl Alcohols: Synthesis of 2,5-Dihydrofurans
    Lv, Xinxin
    Yang, Haijian
    Shi, Taoda
    Xing, Dong
    Xu, Xinfang
    Hu, Wenhao
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1265 - 1270
  • [22] Sulfoxonium-Ylide-Directed C-H Activation and Tandem (4+1) Annulation
    Hanchate, Vinayak
    Devarajappa, Ravi
    Prabhu, Kandikere Ramaiah
    ORGANIC LETTERS, 2020, 22 (08) : 2878 - 2882
  • [23] Stereocontrolled [4+1] Annulation of -Hydroxycyclobutenones: Synthesis of Polysubstituted Cyclopentenones
    Mao, Xu
    Song, Peidong
    Hao, Yu
    Sun, Zezhong
    Hu, Xiangdong
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) : 3719 - 3723
  • [24] Formal [4+1] Annulation of α-Arylhydrazonoketones and Dimethylsulfoxonium Methylide: One-pot Synthesis of Substituted Pyrazoles and Dihydropyrazoles
    Zhang, Qian
    Yu, Mangfei
    Yuan, Jingwen
    Zhang, Rui
    Liang, Yongjiu
    Tian, Jiamei
    Dong, Dewen
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (14): : 6036 - 6041
  • [25] Enantioselective Synthesis of Dihydropyrazoles by Formal [4+1] Cycloaddition of in Situ-Derived Azoalkenes and Sulfur Ylides
    Chen, Jia-Rong
    Dong, Wan-Rong
    Candy, Mathieu
    Pan, Fang-Fang
    Joerres, Manuel
    Bolm, Carsten
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (16) : 6924 - 6927
  • [26] Enantioselective synthesis of dihydropyrazoles by formal [4+1] cycloaddition of in situ-derived azoalkenes and sulfur ylides
    Key Laboratory of Pesticide and Chemical Biology, Central China Normal University, Ministry of Education, 152 Luoyu Road, Wuhan, Hubei 430079, China
    不详
    不详
    J. Am. Chem. Soc., 2012, 16 (6924-6927):
  • [27] SYNTHESIS OF OPTICALLY-ACTIVE SUBSTITUTED DIHYDROFURANS AND DIHYDROPYRROLES VIA PALLADIUM(II)-PROMOTED DIASTEREOSELECTIVE DEHYDROXYLATIVE HETEROCYCLIZATION
    SAITO, S
    HARA, T
    TAKAHASHI, N
    HIRAI, M
    MORIWAKE, T
    SYNLETT, 1992, (03) : 237 - 238
  • [28] Organocatalytic Enantioselective Synthesis of Chiral Spiro-indoline-pyrazolones through a formal [4+1] Annulation Reaction of 4-Bromopyrazolones and aza-ortho-Quinone Methides
    Carceller-Ferrer, Laura
    Rodriguez-Arias, Carlos
    Montesinos-Magraner, Marc
    Sanz-Marco, Amparo
    Hostalet-Romero, Judit
    Blay, Gonzalo
    Pedro, Jose R.
    Vila, Carlos
    HELVETICA CHIMICA ACTA, 2024, 107 (04)
  • [29] Synthesis of 2,5-Dihydrofurans via a Gold(I)-Catalyzed Formal [4+1] Cycloaddition of α-Diazoesters and Propargyl Alcohols
    Wang, Jing
    Yao, Xinbo
    Wang, Tao
    Han, Jie
    Zhang, Jin
    Zhang, Xi
    Wang, Ping
    Zhang, Zunting
    ORGANIC LETTERS, 2015, 17 (20) : 5124 - 5127
  • [30] Enantioselective [4+1] Annulation Reactions of α-Substituted Ammonium Ylides To Construct Spirocyclic Oxindoles
    Zheng, Peng-Fei
    Ouyang, Qin
    Niu, Sheng-Li
    Shuai, Li
    Yuan, Yi
    Jiang, Kun
    Liu, Tian-Yu
    Chen, Ying-Chun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) : 9390 - 9399