Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters

被引:191
作者
Chen, Wen-Bing [1 ,3 ]
Wu, Zhi-Jun [2 ]
Hu, Jing [1 ]
Cun, Lin-Feng [1 ]
Zhang, Xiao-Mei [1 ]
Yuan, Wei-Cheng [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYTIC ENANTIOSELECTIVE SYNTHESIS; ALPHA-ISOTHIOCYANATO IMIDES; QUATERNARY STEREOCENTERS; CRUCIFEROUS PHYTOALEXIN; ENANTIOMERIC ENRICHMENT; STRESS METABOLITES; TERTIARY ALCOHOLS; ACID-DERIVATIVES; ALLENIC ESTERS; AMINO-ACIDS;
D O I
10.1021/ol200724q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of a direct catalytic asymmetric intermolecular aldol reaction of 3-isothiocyanato oxindoles to simple ketones with bifunctional thiourea-tertiary amine as catalyst is reported. This strategy provides a promising approach for the asymmetric synthesis of a range of enantioenriched spirocyclic oxindoles bearing two highly congested contiguous tetrasubstituted carbon stereocenters. Versatile transformations of the spirocyclic oxindole products into other structurally diverse spirocyclic oxindoles have also been demonstrated.
引用
收藏
页码:2472 / 2475
页数:4
相关论文
共 60 条
  • [1] Catalytic Enantioselective Aldol Additions to Ketones
    Adachi, Shinya
    Harada, Toshiro
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (22) : 3661 - 3671
  • [2] Direct catalytic asymmetric aldol reactions of aldehydes
    Bogevig, A
    Kumaragurubaran, N
    Jorgensen, KA
    [J]. CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
  • [3] Carreira E. M., 2000, CATALYTIC ASYMMETRIC
  • [4] Highly Enantioselective Construction of Spiro[4H-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine
    Chen, Wen-Bing
    Wu, Zhi-Jun
    Pei, Qing-Lan
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    [J]. ORGANIC LETTERS, 2010, 12 (14) : 3132 - 3135
  • [5] Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine
    Chen, Wen-Bing
    Du, Xi-Lin
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    [J]. TETRAHEDRON, 2010, 66 (07) : 1441 - 1446
  • [6] Efficient Synthesis of β-Hydroxy-α-Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imide with Aldehydes
    Chen, Xiaohong
    Zhu, Yin
    Qiao, Zhen
    Xie, Mingsheng
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) : 10124 - 10129
  • [7] Enantioselective catalytic formation of quaternary stereogenic centers
    Cozzi, Pier Giorgio
    Hilgraf, Robert
    Zimmermann, Nicole
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) : 5969 - 5994
  • [8] Direct catalytic enantioselective mannich reactions:: Synthesis of protected anti-α,β-diamino acids
    Cutting, Gary A.
    Stainforth, Nikki E.
    John, Matthew P.
    Kociok-Koehn, Gabriele
    Willis, Michael C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (35) : 10632 - +
  • [9] Recent advances in aldolase-catalyzed asymmetric synthesis
    Dean, Stephen M.
    Greenberg, William A.
    Wong, Chi-Huey
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (8-9) : 1308 - 1320
  • [10] Lewis base catalyzed, enantioselective aldol addition of methyl trichlorosilyl ketene acetal to ketones
    Denmark, SE
    Fan, Y
    Eastgate, MD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) : 5235 - 5248