Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines

被引:48
作者
Osborne, Charlotte A. [1 ]
Endean, Thomas B. D. [1 ]
Jarvo, Elizabeth R. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
ASYMMETRIC ARYLATION; CYCLIC IMINES; ALLYLATION; CONSTRUCTION; EFFICIENT; ALLENYLATION; KETIMINES; KETONES; ISOMERIZATION; COMPLEXES;
D O I
10.1021/acs.orglett.5b02692
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective silver-catalyzed propargylation of N-sulfonylketimines is described. This reaction proceeds in high yield and excellent enantiomeric ratio and is compatible with a wide variety of diaryl-and alkylketimines. Synthetic transformations of homopropargylic products via enyne ring-closing metathesis, Sonogashira cross-coupling, and reduction reactions proceed with high stereochemical fidelity. Both allenyl and propargyl borolane reagents can be used to obtain homopropargylic products, a distribution most consistent with a mechanism involving transmetalation of the silver catalyst with the borolane reagent.
引用
收藏
页码:5340 / 5343
页数:4
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共 46 条
  • [1] Zn-mediated asymmetric allylation of N-tert-butanesulfinyl ketimines: an efficient and practical access to chiral quaternary 3-aminooxindoles
    Chen, Diao
    Xu, Ming-Hua
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (13) : 1327 - 1329
  • [2] CHEMISTRY OF OXAZIRIDINES .13. SYNTHESIS, REACTIONS, AND PROPERTIES OF 3-SUBSTITUTED 1,2-BENZISOTHIAZOLE 1,1-DIOXIDE OXIDES
    DAVIS, FA
    TOWSON, JC
    VASHI, DB
    THIMMAREDDY, R
    MCCAULEY, JP
    HARAKAL, ME
    GOSCINIAK, DJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) : 1254 - 1261
  • [3] Catalytic Asymmetric Propargylation
    Ding, Chang-Hua
    Hou, Xue-Long
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1914 - 1937
  • [4] Enyne metathesis (enyne bond reorganization)
    Diver, ST
    Giessert, AJ
    [J]. CHEMICAL REVIEWS, 2004, 104 (03) : 1317 - 1382
  • [5] SYNTHESIS, STRUCTURE, AND REACTIVITY OF SOME (OMICRON-ALLENYL)PALLADIUM(II) AND (OMICRON-PROP-2-YNYL)PALLADIUM(II) COMPLEXES
    ELSEVIER, CJ
    KLEIJN, H
    BOERSMA, J
    VERMEER, P
    [J]. ORGANOMETALLICS, 1986, 5 (04) : 716 - 720
  • [6] Zinc-Catalyzed Allenylations of Aldehydes and Ketones
    Fandrick, Daniel R.
    Saha, Jaideep
    Fandrick, Keith R.
    Sanyal, Sanjit
    Ogikubo, Junichi
    Lee, Heewon
    Roschangar, Frank
    Song, Jinhua J.
    Senanayake, Chris H.
    [J]. ORGANIC LETTERS, 2011, 13 (20) : 5616 - 5619
  • [7] Highly Diastereoselective Zinc-Catalyzed Propargylation of tert-Butanesulfinyl Imines
    Fandrick, Daniel R.
    Johnson, Courtney S.
    Fandrick, Keith R.
    Reeves, Jonathan T.
    Tan, Zhulin
    Lee, Heewon
    Song, Jinhua J.
    Yee, Nathan K.
    Senanayake, Chris H.
    [J]. ORGANIC LETTERS, 2010, 12 (04) : 748 - 751
  • [8] Copper-Catalyst-Controlled Site-Selective Allenylation of Ketones and Aldehydes with Propargyl Boronates
    Fandrick, Keith R.
    Ogikubo, Junichi
    Fandrick, Daniel R.
    Patel, Nitinchandra D.
    Saha, Jaideep
    Lee, Heewon
    Ma, Shengli
    Grinberg, Nelu
    Busacca, Carl A.
    Senanayake, Chris H.
    [J]. ORGANIC LETTERS, 2013, 15 (06) : 1214 - 1217
  • [9] β-silylated homopropargylic amines via the asymmetric allenylboration of aldimines
    Gonzalez, Ana Z.
    Soderquist, John A.
    [J]. ORGANIC LETTERS, 2007, 9 (06) : 1081 - 1084
  • [10] Highly efficient asymmetric construction of quaternary carbon-containing homoallylic and homopropargylic amines
    Guo, Tao
    Song, Ran
    Yuan, Bin-Hua
    Chen, Xiao-Yang
    Sun, Xing-Wen
    Lin, Guo-Qiang
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (47) : 5402 - 5404