Enantioselective allylation of ketones catalyzed by chiral In(III)-PYBOX complexes

被引:55
|
作者
Lu, J
Hong, ML
Ji, SJ [1 ]
Teo, YC
Loh, TP
机构
[1] Suzhou Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215006, Peoples R China
[2] Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore
[3] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
D O I
10.1039/b507768k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of 20 mol% of chiral catalytic complex prepared from In(OTf)(3) and chiral PYBOX, allyltributylstannane reacted with achiral ketones to afford the corresponding homoallylic alcohols in moderate to high enantioselectivities (54-95 % ee), which constitutes the first example of enantioselective allylation of ketones catalyzed by the chiral In(III)-PYBOX complex.
引用
收藏
页码:4217 / 4218
页数:2
相关论文
共 50 条
  • [31] Highly Enantioselective Carbonyl-ene Reactions Catalyzed by In(III)-PyBox Complex
    Zhao, Jun-Feng
    Tsui, Hoi-Yan
    Wu, Pei-Jia
    Lu, Jun
    Loh, Teck-Peng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) : 16492 - +
  • [32] A Spirocyclic Chiral Borate for Catalytic Enantioselective Nozaki-Hiyama Allylation of Ketones
    Huang, Xin-Ren
    Chen, Chinpiao
    Lee, Gene-Hsian
    Peng, Shie-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3089 - 3095
  • [33] Scandium(III)-Catalyzed Enantioselective Allylation of Isatins Using Allylsilanes
    Hanhan, Nadine V.
    Tang, Yng C.
    Tran, Ngon T.
    Franz, Annaliese K.
    ORGANIC LETTERS, 2012, 14 (09) : 2218 - 2221
  • [34] Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Enantiopure Osmium(II) Pybox Complexes
    Vega, Esmeralda
    Lastra, E.
    Gamasa, M. Pilar
    INORGANIC CHEMISTRY, 2013, 52 (10) : 6193 - 6198
  • [35] Highly enantioselective allylation of arylaldehydes catalyzed by a silver(I)-chiral binaphthylthiophosphoramide
    Wang, CJ
    Shi, M
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) : 2823 - 2828
  • [36] Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions
    Kang, Ki-Tae
    Park, Sang Hyun
    Ryu, Do Hyun
    ORGANIC LETTERS, 2019, 21 (17) : 6679 - 6683
  • [37] ENANTIOSELECTIVE TRANSFER HYDROGENATION OF KETONES CATALYZED BY RHODIUM(I) COMPLEXES OF CHIRAL SCHIFF-BASES
    ZASSINOVICH, G
    GRISONI, F
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 247 (02) : C24 - C26
  • [38] Rhodium-Catalyzed Regio- and Enantioselective Direct Allylation of Methyl Ketones
    Li, Bing
    Li, Changkun
    SYNLETT, 2022, 33 (18) : 1863 - 1867
  • [39] Catalytic enantioselective Mukaiyama aldol reaction via a chiral indium(III)-pybox complex
    Fu, Fan
    Teo, Yong-Chua
    Loh, Teck-Peng
    TETRAHEDRON LETTERS, 2006, 47 (25) : 4267 - 4269
  • [40] In(III)-pybox complex catalyzed enantioselective Mukaiyama aldol reactions between polymeric or hydrated glyoxylates and enolsilanes derived from aryl ketones
    Zhao, Jun-Feng
    Tan, Boon-Hong
    Loh, Teck-Peng
    CHEMICAL SCIENCE, 2011, 2 (02) : 349 - 352