Chiral iminophosphorane catalyzed asymmetric sulfenylation of 4-substituted pyrazolones

被引:28
|
作者
Han, Jianwei [1 ,2 ]
Zhang, Yanxia [1 ,2 ]
Wu, Xin-Yan [1 ]
Wong, Henry N. C. [2 ]
机构
[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Lingling Rd, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
MICHAEL ADDITION; STEREOCONTROLLED CONSTRUCTION; ENANTIOSELECTIVITY; PYRAZOL-5-ONES; TEMPERATURE; ALKYLATION; QUATERNARY; PYRAZOLIN-5-ONES; PALLADIUM; KETONES;
D O I
10.1039/c8cc09049a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An excellent level of enantioselectivity in asymmetric sulfenylation of 4-substituted pyrazolones was achieved with chiral iminophosphorane as the organocatalyst under continuum solvation conditions (up to 99% ee). Importantly, this catalytic process features high efficiency with excellent enantioselectivities, easy separation of products, low catalytic loadings and scale-up to grams without loss of enantioselectivity.
引用
收藏
页码:397 / 400
页数:4
相关论文
共 50 条
  • [31] Desymmetrization of 4-substituted cyclohexanones to novel axially chiral oximes
    Nimmagadda, Sri
    Antilla, Jon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [32] Chiral Primary Amine Catalyzed Asymmetric Epoxidation of α-Substituted Acroleins
    Li, Jiuyuan
    Fu, Niankai
    Zhang, Long
    Zhou, Pengxin
    Luo, Sanzhong
    Cheng, Jin-Pei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (35) : 6840 - 6849
  • [33] Asymmetric synthesis of chiral 4-substituted 5,5-diethyl oxazolidin-2-ones as potential effective chiral auxiliaries
    Li, JF
    Yang, R
    Nie, L
    Yang, LJ
    Huang, R
    Lin, J
    JOURNAL OF PEPTIDE RESEARCH, 2005, 66 (06): : 319 - 323
  • [34] ASYMMETRIC-SYNTHESIS VIA CHIRAL HYDROXYLAMINES - SYNTHESIS OF OPTICALLY PURE 4-SUBSTITUTED 2-AZETIDINONES
    BALDWIN, SW
    AUBE, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 186 (AUG): : 179 - ORGN
  • [35] CHIRAL SULFOXIDES IN ASYMMETRIC-SYNTHESIS - A NEW CHIRAL SYNTHESIS OF OPTICALLY-ACTIVE 4-SUBSTITUTED CYCLOHEXYLIDENEACETIC ACID-ESTERS
    SOLLADIE, G
    ZIMMERMANN, R
    BARTSCH, R
    WALBORSKY, HM
    SYNTHESIS-STUTTGART, 1985, (6-7): : 662 - 665
  • [36] Asymmetric syntheses of enantiopure 4-substituted pipecolic acid derivatives
    Agami, C
    Bisaro, F
    Comesse, S
    Guesné, S
    Kadouri-Puchot, C
    Morgentin, R
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (12) : 2385 - 2389
  • [37] Enantioselective Intramolecular [2+2] Photocycloaddition Reactions of 4-Substituted Coumarins Catalyzed by a Chiral Lewis Acid
    Brimioulle, Richard
    Guo, Hao
    Bach, Thorsten
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (24) : 7552 - 7560
  • [38] ASYMMETRIC SYNTHESIS OF 4-SUBSTITUTED 2,6-DIOXOPIPERIDINE-3-CARBONITRILE BY USING THIOUREA-CATALYZED ASYMMETRIC MICHAEL ADDITION
    Inokuma, Tsubasa
    Nagamoto, Yuuki
    Sakamoto, Shota
    Miyabe, Hideto
    Takasu, Kiyosei
    Takemoto, Yoshiji
    HETEROCYCLES, 2009, 79 : 573 - 582
  • [39] Dehydrogenative coupling of 4-substituted Pyridines catalyzed by diruthenium complexes
    Kawashima, Takashi
    Takao, Toshiro
    Suzuki, Hiroharu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) : 11006 - +
  • [40] ELECTRONIC SUBSTITUENT EFFECT OF NITROGEN LIGANDS IN CATALYTIC ASYMMETRIC HYDROSILYLATION OF KETONES - CHIRAL 4-SUBSTITUTED BIS(OXAZOLINYL)PYRIDINES
    NISHIYAMA, H
    YAMAGUCHI, S
    KONDO, M
    ITOH, K
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15): : 4306 - 4309