Trimethylsilyl Trifluoromethanesulfonate-Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes

被引:31
作者
Downey, C. Wade [1 ]
Mahoney, Brian D. [1 ]
Lipari, Vincent R. [1 ]
机构
[1] Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
关键词
PROPARGYLIC ALCOHOLS; TERMINAL ALKYNES; ENANTIOSELECTIVE SYNTHESIS; ACETYLENES; KETONES; FACILE; TMSOTF;
D O I
10.1021/jo900102w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.
引用
收藏
页码:2904 / 2906
页数:3
相关论文
共 16 条
  • [1] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
    Anand, NK
    Carreira, EM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) : 9687 - 9688
  • [2] Enantioselective addition of terminal alkynes to aldehydes catalyzed by a Cu(I)-TRAP complex
    Asano, Yohsuke
    Hara, Kenji
    Ito, Hajime
    Sawamura, Masaya
    [J]. ORGANIC LETTERS, 2007, 9 (20) : 3901 - 3904
  • [3] Me2Zn-mediated addition of acetylenes to aldehydes and ketones
    Cozzi, PG
    Rudolph, J
    Bolm, C
    Norrby, PO
    Tomasini, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) : 5733 - 5736
  • [4] One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf
    Downey, C. Wade
    Johnson, Miles W.
    Tracy, Kathryn J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) : 3299 - 3302
  • [5] A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf
    Downey, C. Wade
    Johnson, Miles W.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (20) : 3559 - 3562
  • [6] Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement
    Engel, Douglas A.
    Dudley, Gregory B.
    [J]. ORGANIC LETTERS, 2006, 8 (18) : 4027 - 4029
  • [7] Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes
    Frantz, DE
    Fässler, R
    Carreira, EM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) : 1806 - 1807
  • [8] Highly enantioselective synthesis of γ-hydroxy-α,β-acetylenic esters by asymmetric alkyne addition to aldehydes
    Gao, G
    Wang, Q
    Yu, XQ
    Xie, RG
    Pu, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (01) : 122 - 125
  • [9] A new halopropargylation of alkynes promoted by boron trihalides.: Highly stereo- and regioselective syntheses of substituted (Z)-1-halo-1,4-enyne derivatives
    Kabalka, GW
    Wu, ZZ
    Ju, YH
    [J]. ORGANIC LETTERS, 2004, 6 (22) : 3929 - 3931
  • [10] Lee KY, 2005, B KOR CHEM SOC, V26, P1617